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carboxylic acid derivatives

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ester protecting groups
ester protecting groups

Behavior under oxidizing conditions

 | peroxycarboxylic acid | sodium hypochlorite estermethyl | stable | moderately reactive methoxymethyl ester | labile | stable methylthiomethyl ester | reactive | reactive tetrahydropyranyl ester | labile | labile benzyloxymethyl ester | labile | stable phenacyl ester | reactive | moderately reactive N-phthalimidomethyl ester | stable | labile 2, 2, 2-trichloroethyl ester | stable | labile 2-haloethyl ester | stable | labile 2-(p-toluenesulfonyl)ethyl ester | stable | labile t-butyl ester | labile | stable cinnamyl ester | reactive | labile benzyl ester | stable | moderately reactive triphenylmethyl ester | labile | moderately reactive bis(o-nitrophenyl)methyl ester | stable | moderately reactive 9-anthrylmethyl ester | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | moderately reactive piperonyl ester | stable | moderately reactive trimethylsilyl ester | labile | labile t-butyldimethylsilyl ester | labile | labile S-t-butyl ester | moderately reactive | labile 2-alkyl-1, 3-oxazolines | reactive | stable  | hydrogen peroxide | chromium trioxide | sodium periodate estermethyl | moderately reactive | stable | stable methoxymethyl ester | stable | labile | stable methylthiomethyl ester | stable | reactive | reactive tetrahydropyranyl ester | moderately reactive | labile | stable benzyloxymethyl ester | stable | labile | stable phenacyl ester | reactive | stable | stable N-phthalimidomethyl ester | labile | stable | stable 2, 2, 2-trichloroethyl ester | moderately reactive | stable | stable 2-haloethyl ester | labile | moderately reactive | stable 2-(p-toluenesulfonyl)ethyl ester | labile | stable | stable t-butyl ester | stable | labile | stable cinnamyl ester | reactive | labile | stable benzyl ester | moderately reactive | stable | stable triphenylmethyl ester | moderately reactive | labile | stable bis(o-nitrophenyl)methyl ester | moderately reactive | stable | stable 9-anthrylmethyl ester | stable | moderately reactive | stable 2-(9, 10-dioxo)anthrylmethyl ester | moderately reactive | stable | stable piperonyl ester | moderately reactive | labile | stable trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | labile | labile | moderately reactive S-t-butyl ester | reactive | moderately reactive | stable 2-alkyl-1, 3-oxazolines | stable | reactive | stable  | selenium dioxide | ozone | dimethyl sulfoxide estermethyl | stable | stable | stable methoxymethyl ester | stable | moderately reactive | stable methylthiomethyl ester | moderately reactive | reactive | moderately reactive tetrahydropyranyl ester | labile | moderately reactive | stable benzyloxymethyl ester | moderately reactive | moderately reactive | stable phenacyl ester | stable | stable | stable N-phthalimidomethyl ester | stable | stable | labile 2, 2, 2-trichloroethyl ester | stable | stable | moderately reactive 2-haloethyl ester | stable | stable | moderately reactive 2-(p-toluenesulfonyl)ethyl ester | stable | stable | moderately reactive t-butyl ester | labile | stable | stable cinnamyl ester | moderately reactive | reactive | stable benzyl ester | moderately reactive | stable | stable triphenylmethyl ester | labile | stable | labile bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | moderately reactive | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | moderately reactive | stable | stable piperonyl ester | moderately reactive | stable | stable trimethylsilyl ester | labile | stable | labile t-butyldimethylsilyl ester | labile | stable | labile S-t-butyl ester | stable | reactive | moderately reactive 2-alkyl-1, 3-oxazolines | moderately reactive | stable | stable  | potassium hexacyanoferrate(III) | lead(IV) cation | lead(IV) cation estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | labile methylthiomethyl ester | stable | reactive | reactive tetrahydropyranyl ester | stable | stable | labile benzyloxymethyl ester | stable | stable | labile phenacyl ester | stable | stable | stable N-phthalimidomethyl ester | labile | stable | stable 2, 2, 2-trichloroethyl ester | moderately reactive | stable | stable 2-haloethyl ester | stable | stable | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable | moderately reactive t-butyl ester | stable | stable | labile cinnamyl ester | stable | stable | moderately reactive benzyl ester | stable | stable | stable triphenylmethyl ester | stable | stable | labile bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | stable piperonyl ester | stable | stable | reactive trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | labile | labile | labile S-t-butyl ester | stable | stable | reactive 2-alkyl-1, 3-oxazolines | stable | stable | reactive  | N-bromosuccinimide/water | bromine/chlorine | manganese dioxide/methylene chloride estermethyl | stable | stable | stable methoxymethyl ester | stable | reactive | stable methylthiomethyl ester | reactive | reactive | stable tetrahydropyranyl ester | stable | moderately reactive | stable benzyloxymethyl ester | stable | reactive | stable phenacyl ester | reactive | reactive | stable N-phthalimidomethyl ester | stable | stable | stable 2, 2, 2-trichloroethyl ester | stable | stable | stable 2-haloethyl ester | stable | stable | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable | stable t-butyl ester | stable | stable | stable cinnamyl ester | reactive | reactive | stable benzyl ester | stable | stable | stable triphenylmethyl ester | stable | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | moderately reactive | stable piperonyl ester | stable | moderately reactive | stable trimethylsilyl ester | labile | stable | stable t-butyldimethylsilyl ester | moderately reactive | stable | stable S-t-butyl ester | labile | reactive | stable 2-alkyl-1, 3-oxazolines | stable | reactive | stable
| peroxycarboxylic acid | sodium hypochlorite estermethyl | stable | moderately reactive methoxymethyl ester | labile | stable methylthiomethyl ester | reactive | reactive tetrahydropyranyl ester | labile | labile benzyloxymethyl ester | labile | stable phenacyl ester | reactive | moderately reactive N-phthalimidomethyl ester | stable | labile 2, 2, 2-trichloroethyl ester | stable | labile 2-haloethyl ester | stable | labile 2-(p-toluenesulfonyl)ethyl ester | stable | labile t-butyl ester | labile | stable cinnamyl ester | reactive | labile benzyl ester | stable | moderately reactive triphenylmethyl ester | labile | moderately reactive bis(o-nitrophenyl)methyl ester | stable | moderately reactive 9-anthrylmethyl ester | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | moderately reactive piperonyl ester | stable | moderately reactive trimethylsilyl ester | labile | labile t-butyldimethylsilyl ester | labile | labile S-t-butyl ester | moderately reactive | labile 2-alkyl-1, 3-oxazolines | reactive | stable | hydrogen peroxide | chromium trioxide | sodium periodate estermethyl | moderately reactive | stable | stable methoxymethyl ester | stable | labile | stable methylthiomethyl ester | stable | reactive | reactive tetrahydropyranyl ester | moderately reactive | labile | stable benzyloxymethyl ester | stable | labile | stable phenacyl ester | reactive | stable | stable N-phthalimidomethyl ester | labile | stable | stable 2, 2, 2-trichloroethyl ester | moderately reactive | stable | stable 2-haloethyl ester | labile | moderately reactive | stable 2-(p-toluenesulfonyl)ethyl ester | labile | stable | stable t-butyl ester | stable | labile | stable cinnamyl ester | reactive | labile | stable benzyl ester | moderately reactive | stable | stable triphenylmethyl ester | moderately reactive | labile | stable bis(o-nitrophenyl)methyl ester | moderately reactive | stable | stable 9-anthrylmethyl ester | stable | moderately reactive | stable 2-(9, 10-dioxo)anthrylmethyl ester | moderately reactive | stable | stable piperonyl ester | moderately reactive | labile | stable trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | labile | labile | moderately reactive S-t-butyl ester | reactive | moderately reactive | stable 2-alkyl-1, 3-oxazolines | stable | reactive | stable | selenium dioxide | ozone | dimethyl sulfoxide estermethyl | stable | stable | stable methoxymethyl ester | stable | moderately reactive | stable methylthiomethyl ester | moderately reactive | reactive | moderately reactive tetrahydropyranyl ester | labile | moderately reactive | stable benzyloxymethyl ester | moderately reactive | moderately reactive | stable phenacyl ester | stable | stable | stable N-phthalimidomethyl ester | stable | stable | labile 2, 2, 2-trichloroethyl ester | stable | stable | moderately reactive 2-haloethyl ester | stable | stable | moderately reactive 2-(p-toluenesulfonyl)ethyl ester | stable | stable | moderately reactive t-butyl ester | labile | stable | stable cinnamyl ester | moderately reactive | reactive | stable benzyl ester | moderately reactive | stable | stable triphenylmethyl ester | labile | stable | labile bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | moderately reactive | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | moderately reactive | stable | stable piperonyl ester | moderately reactive | stable | stable trimethylsilyl ester | labile | stable | labile t-butyldimethylsilyl ester | labile | stable | labile S-t-butyl ester | stable | reactive | moderately reactive 2-alkyl-1, 3-oxazolines | moderately reactive | stable | stable | potassium hexacyanoferrate(III) | lead(IV) cation | lead(IV) cation estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | labile methylthiomethyl ester | stable | reactive | reactive tetrahydropyranyl ester | stable | stable | labile benzyloxymethyl ester | stable | stable | labile phenacyl ester | stable | stable | stable N-phthalimidomethyl ester | labile | stable | stable 2, 2, 2-trichloroethyl ester | moderately reactive | stable | stable 2-haloethyl ester | stable | stable | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable | moderately reactive t-butyl ester | stable | stable | labile cinnamyl ester | stable | stable | moderately reactive benzyl ester | stable | stable | stable triphenylmethyl ester | stable | stable | labile bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | stable piperonyl ester | stable | stable | reactive trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | labile | labile | labile S-t-butyl ester | stable | stable | reactive 2-alkyl-1, 3-oxazolines | stable | stable | reactive | N-bromosuccinimide/water | bromine/chlorine | manganese dioxide/methylene chloride estermethyl | stable | stable | stable methoxymethyl ester | stable | reactive | stable methylthiomethyl ester | reactive | reactive | stable tetrahydropyranyl ester | stable | moderately reactive | stable benzyloxymethyl ester | stable | reactive | stable phenacyl ester | reactive | reactive | stable N-phthalimidomethyl ester | stable | stable | stable 2, 2, 2-trichloroethyl ester | stable | stable | stable 2-haloethyl ester | stable | stable | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable | stable t-butyl ester | stable | stable | stable cinnamyl ester | reactive | reactive | stable benzyl ester | stable | stable | stable triphenylmethyl ester | stable | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | moderately reactive | stable piperonyl ester | stable | moderately reactive | stable trimethylsilyl ester | labile | stable | stable t-butyldimethylsilyl ester | moderately reactive | stable | stable S-t-butyl ester | labile | reactive | stable 2-alkyl-1, 3-oxazolines | stable | reactive | stable

Behavior under reducing conditions

 | lithium aluminum hydride | diisobutylaluminum hydride | lithium tri-tert-butoxyaluminum hydride estermethyl | reactive | reactive | moderately reactive methoxymethyl ester | reactive | reactive | moderately reactive methylthiomethyl ester | reactive | reactive | moderately reactive tetrahydropyranyl ester | reactive | reactive | moderately reactive benzyloxymethyl ester | reactive | reactive | moderately reactive phenacyl ester | reactive | reactive | moderately reactive N-phthalimidomethyl ester | reactive | reactive | stable 2, 2, 2-trichloroethyl ester | reactive | reactive | moderately reactive 2-haloethyl ester | reactive | reactive | moderately reactive 2-(p-toluenesulfonyl)ethyl ester | reactive | reactive | moderately reactive t-butyl ester | reactive | stable | stable cinnamyl ester | reactive | reactive | moderately reactive benzyl ester | reactive | reactive | moderately reactive triphenylmethyl ester | reactive | reactive | stable bis(o-nitrophenyl)methyl ester | reactive | reactive | moderately reactive 9-anthrylmethyl ester | reactive | reactive | moderately reactive 2-(9, 10-dioxo)anthrylmethyl ester | reactive | reactive | moderately reactive piperonyl ester | reactive | reactive | moderately reactive trimethylsilyl ester | reactive | reactive | labile t-butyldimethylsilyl ester | reactive | reactive | moderately reactive S-t-butyl ester | reactive | reactive | moderately reactive 2-alkyl-1, 3-oxazolines | stable | moderately reactive | stable  | sodium borohydride | zinc borohydride | L-selectride estermethyl | stable | stable | moderately reactive methoxymethyl ester | stable | stable | moderately reactive methylthiomethyl ester | stable | stable | moderately reactive tetrahydropyranyl ester | stable | stable | moderately reactive benzyloxymethyl ester | stable | stable | moderately reactive phenacyl ester | moderately reactive | moderately reactive | reactive N-phthalimidomethyl ester | stable | stable | moderately reactive 2, 2, 2-trichloroethyl ester | stable | stable | moderately reactive 2-haloethyl ester | stable | stable | moderately reactive 2-(p-toluenesulfonyl)ethyl ester | stable | stable | moderately reactive t-butyl ester | stable | stable | stable cinnamyl ester | stable | stable | moderately reactive benzyl ester | stable | stable | moderately reactive triphenylmethyl ester | stable | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable | moderately reactive 9-anthrylmethyl ester | stable | stable | moderately reactive 2-(9, 10-dioxo)anthrylmethyl ester | moderately reactive | moderately reactive | reactive piperonyl ester | stable | stable | moderately reactive trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | stable | stable | moderately reactive S-t-butyl ester | stable | stable | moderately reactive 2-alkyl-1, 3-oxazolines | stable | stable | stable  | disiamylborane | sodium cyanoborohydride | diborane estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | stable methylthiomethyl ester | stable | stable | stable tetrahydropyranyl ester | stable | stable | stable benzyloxymethyl ester | stable | stable | stable phenacyl ester | reactive | stable | reactive N-phthalimidomethyl ester | reactive | stable | reactive 2, 2, 2-trichloroethyl ester | stable | stable | stable 2-haloethyl ester | stable | reactive | stable 2-(p-toluenesulfonyl)ethyl ester | stable | reactive | stable t-butyl ester | stable | stable | stable cinnamyl ester | reactive | stable | reactive benzyl ester | stable | stable | stable triphenylmethyl ester | stable | moderately reactive | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | moderately reactive | stable | moderately reactive piperonyl ester | stable | stable | stable trimethylsilyl ester | labile | labile | reactive t-butyldimethylsilyl ester | stable | labile | stable S-t-butyl ester | stable | stable | stable 2-alkyl-1, 3-oxazolines | moderately reactive | moderately reactive | stable  | aluminium amalgam | hydrogen/nickel | hydrogen/rhodium estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | stable methylthiomethyl ester | stable | reactive | reactive tetrahydropyranyl ester | stable | stable | stable benzyloxymethyl ester | stable | labile | moderately reactive phenacyl ester | reactive | labile | moderately reactive N-phthalimidomethyl ester | stable | stable | moderately reactive 2, 2, 2-trichloroethyl ester | moderately reactive | reactive | stable 2-haloethyl ester | moderately reactive | reactive | stable 2-(p-toluenesulfonyl)ethyl ester | moderately reactive | reactive | stable t-butyl ester | stable | stable | stable cinnamyl ester | stable | reactive | reactive benzyl ester | stable | labile | stable triphenylmethyl ester | stable | labile | moderately reactive bis(o-nitrophenyl)methyl ester | reactive | reactive | reactive 9-anthrylmethyl ester | stable | labile | moderately reactive 2-(9, 10-dioxo)anthrylmethyl ester | reactive | labile | moderately reactive piperonyl ester | stable | labile | moderately reactive trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | stable | stable | stable S-t-butyl ester | stable | reactive | reactive 2-alkyl-1, 3-oxazolines | moderately reactive | reactive | reactive  | hydrogen/palladium | sodium/ammonia estermethyl | stable | reactive methoxymethyl ester | stable | reactive methylthiomethyl ester | reactive | reactive tetrahydropyranyl ester | stable | reactive benzyloxymethyl ester | labile | reactive phenacyl ester | labile | reactive N-phthalimidomethyl ester | stable | reactive 2, 2, 2-trichloroethyl ester | stable | reactive 2-haloethyl ester | reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | stable | reactive t-butyl ester | stable | reactive cinnamyl ester | reactive | reactive benzyl ester | labile | labile triphenylmethyl ester | labile | reactive bis(o-nitrophenyl)methyl ester | reactive | labile 9-anthrylmethyl ester | labile | labile 2-(9, 10-dioxo)anthrylmethyl ester | labile | labile piperonyl ester | labile | labile trimethylsilyl ester | labile | reactive t-butyldimethylsilyl ester | stable | reactive S-t-butyl ester | reactive | reactive 2-alkyl-1, 3-oxazolines | reactive | reactive  | stannous chloride/pyridine | hydrogen/platinum estermethyl | stable | stable methoxymethyl ester | stable | stable methylthiomethyl ester | stable | reactive tetrahydropyranyl ester | stable | labile benzyloxymethyl ester | stable | labile phenacyl ester | stable | labile N-phthalimidomethyl ester | stable | moderately reactive 2, 2, 2-trichloroethyl ester | stable | reactive 2-haloethyl ester | moderately reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | moderately reactive | stable t-butyl ester | stable | stable cinnamyl ester | stable | reactive benzyl ester | stable | labile triphenylmethyl ester | stable | labile bis(o-nitrophenyl)methyl ester | stable | reactive 9-anthrylmethyl ester | stable | labile 2-(9, 10-dioxo)anthrylmethyl ester | moderately reactive | labile piperonyl ester | stable | labile trimethylsilyl ester | stable | labile t-butyldimethylsilyl ester | stable | labile S-t-butyl ester | stable | reactive 2-alkyl-1, 3-oxazolines | stable | reactive
| lithium aluminum hydride | diisobutylaluminum hydride | lithium tri-tert-butoxyaluminum hydride estermethyl | reactive | reactive | moderately reactive methoxymethyl ester | reactive | reactive | moderately reactive methylthiomethyl ester | reactive | reactive | moderately reactive tetrahydropyranyl ester | reactive | reactive | moderately reactive benzyloxymethyl ester | reactive | reactive | moderately reactive phenacyl ester | reactive | reactive | moderately reactive N-phthalimidomethyl ester | reactive | reactive | stable 2, 2, 2-trichloroethyl ester | reactive | reactive | moderately reactive 2-haloethyl ester | reactive | reactive | moderately reactive 2-(p-toluenesulfonyl)ethyl ester | reactive | reactive | moderately reactive t-butyl ester | reactive | stable | stable cinnamyl ester | reactive | reactive | moderately reactive benzyl ester | reactive | reactive | moderately reactive triphenylmethyl ester | reactive | reactive | stable bis(o-nitrophenyl)methyl ester | reactive | reactive | moderately reactive 9-anthrylmethyl ester | reactive | reactive | moderately reactive 2-(9, 10-dioxo)anthrylmethyl ester | reactive | reactive | moderately reactive piperonyl ester | reactive | reactive | moderately reactive trimethylsilyl ester | reactive | reactive | labile t-butyldimethylsilyl ester | reactive | reactive | moderately reactive S-t-butyl ester | reactive | reactive | moderately reactive 2-alkyl-1, 3-oxazolines | stable | moderately reactive | stable | sodium borohydride | zinc borohydride | L-selectride estermethyl | stable | stable | moderately reactive methoxymethyl ester | stable | stable | moderately reactive methylthiomethyl ester | stable | stable | moderately reactive tetrahydropyranyl ester | stable | stable | moderately reactive benzyloxymethyl ester | stable | stable | moderately reactive phenacyl ester | moderately reactive | moderately reactive | reactive N-phthalimidomethyl ester | stable | stable | moderately reactive 2, 2, 2-trichloroethyl ester | stable | stable | moderately reactive 2-haloethyl ester | stable | stable | moderately reactive 2-(p-toluenesulfonyl)ethyl ester | stable | stable | moderately reactive t-butyl ester | stable | stable | stable cinnamyl ester | stable | stable | moderately reactive benzyl ester | stable | stable | moderately reactive triphenylmethyl ester | stable | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable | moderately reactive 9-anthrylmethyl ester | stable | stable | moderately reactive 2-(9, 10-dioxo)anthrylmethyl ester | moderately reactive | moderately reactive | reactive piperonyl ester | stable | stable | moderately reactive trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | stable | stable | moderately reactive S-t-butyl ester | stable | stable | moderately reactive 2-alkyl-1, 3-oxazolines | stable | stable | stable | disiamylborane | sodium cyanoborohydride | diborane estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | stable methylthiomethyl ester | stable | stable | stable tetrahydropyranyl ester | stable | stable | stable benzyloxymethyl ester | stable | stable | stable phenacyl ester | reactive | stable | reactive N-phthalimidomethyl ester | reactive | stable | reactive 2, 2, 2-trichloroethyl ester | stable | stable | stable 2-haloethyl ester | stable | reactive | stable 2-(p-toluenesulfonyl)ethyl ester | stable | reactive | stable t-butyl ester | stable | stable | stable cinnamyl ester | reactive | stable | reactive benzyl ester | stable | stable | stable triphenylmethyl ester | stable | moderately reactive | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | moderately reactive | stable | moderately reactive piperonyl ester | stable | stable | stable trimethylsilyl ester | labile | labile | reactive t-butyldimethylsilyl ester | stable | labile | stable S-t-butyl ester | stable | stable | stable 2-alkyl-1, 3-oxazolines | moderately reactive | moderately reactive | stable | aluminium amalgam | hydrogen/nickel | hydrogen/rhodium estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | stable methylthiomethyl ester | stable | reactive | reactive tetrahydropyranyl ester | stable | stable | stable benzyloxymethyl ester | stable | labile | moderately reactive phenacyl ester | reactive | labile | moderately reactive N-phthalimidomethyl ester | stable | stable | moderately reactive 2, 2, 2-trichloroethyl ester | moderately reactive | reactive | stable 2-haloethyl ester | moderately reactive | reactive | stable 2-(p-toluenesulfonyl)ethyl ester | moderately reactive | reactive | stable t-butyl ester | stable | stable | stable cinnamyl ester | stable | reactive | reactive benzyl ester | stable | labile | stable triphenylmethyl ester | stable | labile | moderately reactive bis(o-nitrophenyl)methyl ester | reactive | reactive | reactive 9-anthrylmethyl ester | stable | labile | moderately reactive 2-(9, 10-dioxo)anthrylmethyl ester | reactive | labile | moderately reactive piperonyl ester | stable | labile | moderately reactive trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | stable | stable | stable S-t-butyl ester | stable | reactive | reactive 2-alkyl-1, 3-oxazolines | moderately reactive | reactive | reactive | hydrogen/palladium | sodium/ammonia estermethyl | stable | reactive methoxymethyl ester | stable | reactive methylthiomethyl ester | reactive | reactive tetrahydropyranyl ester | stable | reactive benzyloxymethyl ester | labile | reactive phenacyl ester | labile | reactive N-phthalimidomethyl ester | stable | reactive 2, 2, 2-trichloroethyl ester | stable | reactive 2-haloethyl ester | reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | stable | reactive t-butyl ester | stable | reactive cinnamyl ester | reactive | reactive benzyl ester | labile | labile triphenylmethyl ester | labile | reactive bis(o-nitrophenyl)methyl ester | reactive | labile 9-anthrylmethyl ester | labile | labile 2-(9, 10-dioxo)anthrylmethyl ester | labile | labile piperonyl ester | labile | labile trimethylsilyl ester | labile | reactive t-butyldimethylsilyl ester | stable | reactive S-t-butyl ester | reactive | reactive 2-alkyl-1, 3-oxazolines | reactive | reactive | stannous chloride/pyridine | hydrogen/platinum estermethyl | stable | stable methoxymethyl ester | stable | stable methylthiomethyl ester | stable | reactive tetrahydropyranyl ester | stable | labile benzyloxymethyl ester | stable | labile phenacyl ester | stable | labile N-phthalimidomethyl ester | stable | moderately reactive 2, 2, 2-trichloroethyl ester | stable | reactive 2-haloethyl ester | moderately reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | moderately reactive | stable t-butyl ester | stable | stable cinnamyl ester | stable | reactive benzyl ester | stable | labile triphenylmethyl ester | stable | labile bis(o-nitrophenyl)methyl ester | stable | reactive 9-anthrylmethyl ester | stable | labile 2-(9, 10-dioxo)anthrylmethyl ester | moderately reactive | labile piperonyl ester | stable | labile trimethylsilyl ester | stable | labile t-butyldimethylsilyl ester | stable | labile S-t-butyl ester | stable | reactive 2-alkyl-1, 3-oxazolines | stable | reactive

Behavior under electrophilic conditions

 | acid chloride | aldehyde estermethyl | stable | stable methoxymethyl ester | stable | stable methylthiomethyl ester | stable | stable tetrahydropyranyl ester | stable | stable benzyloxymethyl ester | stable | stable phenacyl ester | stable | stable N-phthalimidomethyl ester | stable | stable 2, 2, 2-trichloroethyl ester | stable | stable 2-haloethyl ester | stable | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable t-butyl ester | stable | stable cinnamyl ester | stable | stable benzyl ester | stable | stable triphenylmethyl ester | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable 9-anthrylmethyl ester | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable piperonyl ester | stable | stable trimethylsilyl ester | moderately reactive | stable t-butyldimethylsilyl ester | moderately reactive | stable S-t-butyl ester | stable | stable 2-alkyl-1, 3-oxazolines | reactive | stable
| acid chloride | aldehyde estermethyl | stable | stable methoxymethyl ester | stable | stable methylthiomethyl ester | stable | stable tetrahydropyranyl ester | stable | stable benzyloxymethyl ester | stable | stable phenacyl ester | stable | stable N-phthalimidomethyl ester | stable | stable 2, 2, 2-trichloroethyl ester | stable | stable 2-haloethyl ester | stable | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable t-butyl ester | stable | stable cinnamyl ester | stable | stable benzyl ester | stable | stable triphenylmethyl ester | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable 9-anthrylmethyl ester | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable piperonyl ester | stable | stable trimethylsilyl ester | moderately reactive | stable t-butyldimethylsilyl ester | moderately reactive | stable S-t-butyl ester | stable | stable 2-alkyl-1, 3-oxazolines | reactive | stable

Behavior under nucleophilic conditions

 | organolithium | organocopper | enolate estermethyl | reactive | stable | reactive methoxymethyl ester | reactive | stable | reactive methylthiomethyl ester | reactive | stable | reactive tetrahydropyranyl ester | reactive | stable | reactive benzyloxymethyl ester | reactive | stable | reactive phenacyl ester | reactive | stable | reactive N-phthalimidomethyl ester | reactive | stable | reactive 2, 2, 2-trichloroethyl ester | reactive | reactive | reactive 2-haloethyl ester | reactive | reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | reactive | stable | reactive t-butyl ester | reactive | stable | stable cinnamyl ester | reactive | labile | reactive benzyl ester | reactive | stable | reactive triphenylmethyl ester | reactive | stable | reactive bis(o-nitrophenyl)methyl ester | reactive | stable | reactive 9-anthrylmethyl ester | reactive | stable | reactive 2-(9, 10-dioxo)anthrylmethyl ester | reactive | stable | reactive piperonyl ester | reactive | stable | reactive trimethylsilyl ester | reactive | labile | reactive t-butyldimethylsilyl ester | reactive | stable | reactive S-t-butyl ester | reactive | reactive | reactive 2-alkyl-1, 3-oxazolines | stable | stable | stable
| organolithium | organocopper | enolate estermethyl | reactive | stable | reactive methoxymethyl ester | reactive | stable | reactive methylthiomethyl ester | reactive | stable | reactive tetrahydropyranyl ester | reactive | stable | reactive benzyloxymethyl ester | reactive | stable | reactive phenacyl ester | reactive | stable | reactive N-phthalimidomethyl ester | reactive | stable | reactive 2, 2, 2-trichloroethyl ester | reactive | reactive | reactive 2-haloethyl ester | reactive | reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | reactive | stable | reactive t-butyl ester | reactive | stable | stable cinnamyl ester | reactive | labile | reactive benzyl ester | reactive | stable | reactive triphenylmethyl ester | reactive | stable | reactive bis(o-nitrophenyl)methyl ester | reactive | stable | reactive 9-anthrylmethyl ester | reactive | stable | reactive 2-(9, 10-dioxo)anthrylmethyl ester | reactive | stable | reactive piperonyl ester | reactive | stable | reactive trimethylsilyl ester | reactive | labile | reactive t-butyldimethylsilyl ester | reactive | stable | reactive S-t-butyl ester | reactive | reactive | reactive 2-alkyl-1, 3-oxazolines | stable | stable | stable

Behavior under basic conditions

 | potassium tert-butoxide | sodium hydride | sodium amide estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | stable methylthiomethyl ester | stable | stable | stable tetrahydropyranyl ester | stable | stable | stable benzyloxymethyl ester | stable | stable | stable phenacyl ester | moderately reactive | reactive | reactive N-phthalimidomethyl ester | stable | stable | stable 2, 2, 2-trichloroethyl ester | reactive | reactive | reactive 2-haloethyl ester | reactive | reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | reactive | reactive | reactive t-butyl ester | stable | stable | stable cinnamyl ester | stable | stable | stable benzyl ester | stable | stable | stable triphenylmethyl ester | stable | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | stable piperonyl ester | stable | stable | stable trimethylsilyl ester | stable | stable | stable t-butyldimethylsilyl ester | stable | stable | stable S-t-butyl ester | stable | stable | stable 2-alkyl-1, 3-oxazolines | stable | stable | stable  | dimsyl sodium | triphenylmethyl sodium estermethyl | reactive | stable methoxymethyl ester | reactive | stable methylthiomethyl ester | reactive | stable tetrahydropyranyl ester | reactive | stable benzyloxymethyl ester | reactive | stable phenacyl ester | reactive | reactive N-phthalimidomethyl ester | reactive | stable 2, 2, 2-trichloroethyl ester | reactive | reactive 2-haloethyl ester | reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | reactive | reactive t-butyl ester | reactive | stable cinnamyl ester | reactive | stable benzyl ester | reactive | stable triphenylmethyl ester | reactive | stable bis(o-nitrophenyl)methyl ester | reactive | stable 9-anthrylmethyl ester | reactive | stable 2-(9, 10-dioxo)anthrylmethyl ester | reactive | stable piperonyl ester | reactive | stable trimethylsilyl ester | reactive | stable t-butyldimethylsilyl ester | reactive | stable S-t-butyl ester | reactive | stable 2-alkyl-1, 3-oxazolines | stable | stable
| potassium tert-butoxide | sodium hydride | sodium amide estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | stable methylthiomethyl ester | stable | stable | stable tetrahydropyranyl ester | stable | stable | stable benzyloxymethyl ester | stable | stable | stable phenacyl ester | moderately reactive | reactive | reactive N-phthalimidomethyl ester | stable | stable | stable 2, 2, 2-trichloroethyl ester | reactive | reactive | reactive 2-haloethyl ester | reactive | reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | reactive | reactive | reactive t-butyl ester | stable | stable | stable cinnamyl ester | stable | stable | stable benzyl ester | stable | stable | stable triphenylmethyl ester | stable | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | stable piperonyl ester | stable | stable | stable trimethylsilyl ester | stable | stable | stable t-butyldimethylsilyl ester | stable | stable | stable S-t-butyl ester | stable | stable | stable 2-alkyl-1, 3-oxazolines | stable | stable | stable | dimsyl sodium | triphenylmethyl sodium estermethyl | reactive | stable methoxymethyl ester | reactive | stable methylthiomethyl ester | reactive | stable tetrahydropyranyl ester | reactive | stable benzyloxymethyl ester | reactive | stable phenacyl ester | reactive | reactive N-phthalimidomethyl ester | reactive | stable 2, 2, 2-trichloroethyl ester | reactive | reactive 2-haloethyl ester | reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | reactive | reactive t-butyl ester | reactive | stable cinnamyl ester | reactive | stable benzyl ester | reactive | stable triphenylmethyl ester | reactive | stable bis(o-nitrophenyl)methyl ester | reactive | stable 9-anthrylmethyl ester | reactive | stable 2-(9, 10-dioxo)anthrylmethyl ester | reactive | stable piperonyl ester | reactive | stable trimethylsilyl ester | reactive | stable t-butyldimethylsilyl ester | reactive | stable S-t-butyl ester | reactive | stable 2-alkyl-1, 3-oxazolines | stable | stable

Behavior under acidic conditions

 | copper(II) cation/pyridine | silver(I) cation | mercury(II) cation estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | stable methylthiomethyl ester | stable | labile | labile tetrahydropyranyl ester | stable | stable | stable benzyloxymethyl ester | stable | stable | stable phenacyl ester | stable | stable | stable N-phthalimidomethyl ester | stable | stable | stable 2, 2, 2-trichloroethyl ester | stable | reactive | stable 2-haloethyl ester | stable | moderately reactive | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable | stable t-butyl ester | stable | stable | stable cinnamyl ester | stable | stable | reactive benzyl ester | stable | stable | stable triphenylmethyl ester | stable | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | stable piperonyl ester | stable | stable | stable trimethylsilyl ester | stable | labile | labile t-butyldimethylsilyl ester | stable | stable | stable S-t-butyl ester | reactive | reactive | reactive 2-alkyl-1, 3-oxazolines | stable | stable | stable
| copper(II) cation/pyridine | silver(I) cation | mercury(II) cation estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | stable methylthiomethyl ester | stable | labile | labile tetrahydropyranyl ester | stable | stable | stable benzyloxymethyl ester | stable | stable | stable phenacyl ester | stable | stable | stable N-phthalimidomethyl ester | stable | stable | stable 2, 2, 2-trichloroethyl ester | stable | reactive | stable 2-haloethyl ester | stable | moderately reactive | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable | stable t-butyl ester | stable | stable | stable cinnamyl ester | stable | stable | reactive benzyl ester | stable | stable | stable triphenylmethyl ester | stable | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | stable piperonyl ester | stable | stable | stable trimethylsilyl ester | stable | labile | labile t-butyldimethylsilyl ester | stable | stable | stable S-t-butyl ester | reactive | reactive | reactive 2-alkyl-1, 3-oxazolines | stable | stable | stable

Behavior under other conditions

 | nickel carbonyl | diazomethane | trimethyloxonium tetrafluoroborate(1-) estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | stable methylthiomethyl ester | stable | stable | reactive tetrahydropyranyl ester | stable | stable | stable benzyloxymethyl ester | stable | stable | stable phenacyl ester | stable | stable | stable N-phthalimidomethyl ester | stable | stable | reactive 2, 2, 2-trichloroethyl ester | moderately reactive | stable | stable 2-haloethyl ester | stable | stable | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable | stable t-butyl ester | stable | stable | stable cinnamyl ester | reactive | stable | stable benzyl ester | stable | stable | stable triphenylmethyl ester | stable | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | stable piperonyl ester | stable | stable | stable trimethylsilyl ester | stable | stable | labile t-butyldimethylsilyl ester | stable | stable | stable S-t-butyl ester | stable | stable | reactive 2-alkyl-1, 3-oxazolines | stable | stable | reactive
| nickel carbonyl | diazomethane | trimethyloxonium tetrafluoroborate(1-) estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | stable methylthiomethyl ester | stable | stable | reactive tetrahydropyranyl ester | stable | stable | stable benzyloxymethyl ester | stable | stable | stable phenacyl ester | stable | stable | stable N-phthalimidomethyl ester | stable | stable | reactive 2, 2, 2-trichloroethyl ester | moderately reactive | stable | stable 2-haloethyl ester | stable | stable | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable | stable t-butyl ester | stable | stable | stable cinnamyl ester | reactive | stable | stable benzyl ester | stable | stable | stable triphenylmethyl ester | stable | stable | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | stable piperonyl ester | stable | stable | stable trimethylsilyl ester | stable | stable | labile t-butyldimethylsilyl ester | stable | stable | stable S-t-butyl ester | stable | stable | reactive 2-alkyl-1, 3-oxazolines | stable | stable | reactive

Behavior under aqueous conditions

 | strong acid | strong acid (at 100 °C) | pH 1 (at 25 °C) estermethyl | labile | labile | stable methoxymethyl ester | labile | labile | labile methylthiomethyl ester | moderately reactive | labile | stable tetrahydropyranyl ester | labile | labile | labile benzyloxymethyl ester | labile | labile | labile phenacyl ester | stable | labile | stable N-phthalimidomethyl ester | labile | labile | stable 2, 2, 2-trichloroethyl ester | stable | reactive | stable 2-haloethyl ester | labile | labile | moderately reactive 2-(p-toluenesulfonyl)ethyl ester | labile | labile | stable t-butyl ester | labile | labile | labile cinnamyl ester | labile | labile | labile benzyl ester | moderately reactive | labile | stable triphenylmethyl ester | labile | labile | labile bis(o-nitrophenyl)methyl ester | moderately reactive | labile | stable 9-anthrylmethyl ester | labile | labile | moderately reactive 2-(9, 10-dioxo)anthrylmethyl ester | labile | labile | stable piperonyl ester | labile | labile | labile trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | labile | labile | labile S-t-butyl ester | labile | labile | moderately reactive 2-alkyl-1, 3-oxazolines | labile | labile | moderately reactive  | pH 2-4 | pH 4-6 | pH 6-8.5 estermethyl | stable | stable | stable methoxymethyl ester | moderately reactive | stable | stable methylthiomethyl ester | stable | stable | stable tetrahydropyranyl ester | labile | stable | stable benzyloxymethyl ester | moderately reactive | stable | stable phenacyl ester | stable | stable | stable N-phthalimidomethyl ester | stable | stable | stable 2, 2, 2-trichloroethyl ester | stable | stable | stable 2-haloethyl ester | stable | stable | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable | stable t-butyl ester | labile | stable | stable cinnamyl ester | stable | stable | stable benzyl ester | stable | stable | stable triphenylmethyl ester | labile | moderately reactive | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | stable piperonyl ester | stable | stable | stable trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | labile | labile | moderately reactive S-t-butyl ester | stable | stable | stable 2-alkyl-1, 3-oxazolines | stable | stable | stable  | pH 8.5-10 | pH 10-12 estermethyl | stable | moderately reactive methoxymethyl ester | stable | stable methylthiomethyl ester | stable | stable tetrahydropyranyl ester | stable | moderately reactive benzyloxymethyl ester | stable | stable phenacyl ester | stable | moderately reactive N-phthalimidomethyl ester | labile | labile 2, 2, 2-trichloroethyl ester | moderately reactive | labile 2-haloethyl ester | stable | labile 2-(p-toluenesulfonyl)ethyl ester | moderately reactive | labile t-butyl ester | stable | stable cinnamyl ester | stable | labile benzyl ester | stable | labile triphenylmethyl ester | stable | moderately reactive bis(o-nitrophenyl)methyl ester | stable | moderately reactive 9-anthrylmethyl ester | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | moderately reactive piperonyl ester | stable | moderately reactive trimethylsilyl ester | labile | labile t-butyldimethylsilyl ester | labile | labile S-t-butyl ester | stable | stable 2-alkyl-1, 3-oxazolines | stable | stable  | strong base | strong base (at 150 °C) estermethyl | labile | labile methoxymethyl ester | labile | labile methylthiomethyl ester | moderately reactive | labile tetrahydropyranyl ester | labile | labile benzyloxymethyl ester | labile | labile phenacyl ester | labile | labile N-phthalimidomethyl ester | labile | labile 2, 2, 2-trichloroethyl ester | labile | labile 2-haloethyl ester | labile | labile 2-(p-toluenesulfonyl)ethyl ester | labile | labile t-butyl ester | labile | labile cinnamyl ester | labile | labile benzyl ester | labile | labile triphenylmethyl ester | labile | labile bis(o-nitrophenyl)methyl ester | labile | labile 9-anthrylmethyl ester | labile | labile 2-(9, 10-dioxo)anthrylmethyl ester | labile | labile piperonyl ester | labile | labile trimethylsilyl ester | labile | labile t-butyldimethylsilyl ester | labile | labile S-t-butyl ester | moderately reactive | labile 2-alkyl-1, 3-oxazolines | moderately reactive | labile
| strong acid | strong acid (at 100 °C) | pH 1 (at 25 °C) estermethyl | labile | labile | stable methoxymethyl ester | labile | labile | labile methylthiomethyl ester | moderately reactive | labile | stable tetrahydropyranyl ester | labile | labile | labile benzyloxymethyl ester | labile | labile | labile phenacyl ester | stable | labile | stable N-phthalimidomethyl ester | labile | labile | stable 2, 2, 2-trichloroethyl ester | stable | reactive | stable 2-haloethyl ester | labile | labile | moderately reactive 2-(p-toluenesulfonyl)ethyl ester | labile | labile | stable t-butyl ester | labile | labile | labile cinnamyl ester | labile | labile | labile benzyl ester | moderately reactive | labile | stable triphenylmethyl ester | labile | labile | labile bis(o-nitrophenyl)methyl ester | moderately reactive | labile | stable 9-anthrylmethyl ester | labile | labile | moderately reactive 2-(9, 10-dioxo)anthrylmethyl ester | labile | labile | stable piperonyl ester | labile | labile | labile trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | labile | labile | labile S-t-butyl ester | labile | labile | moderately reactive 2-alkyl-1, 3-oxazolines | labile | labile | moderately reactive | pH 2-4 | pH 4-6 | pH 6-8.5 estermethyl | stable | stable | stable methoxymethyl ester | moderately reactive | stable | stable methylthiomethyl ester | stable | stable | stable tetrahydropyranyl ester | labile | stable | stable benzyloxymethyl ester | moderately reactive | stable | stable phenacyl ester | stable | stable | stable N-phthalimidomethyl ester | stable | stable | stable 2, 2, 2-trichloroethyl ester | stable | stable | stable 2-haloethyl ester | stable | stable | stable 2-(p-toluenesulfonyl)ethyl ester | stable | stable | stable t-butyl ester | labile | stable | stable cinnamyl ester | stable | stable | stable benzyl ester | stable | stable | stable triphenylmethyl ester | labile | moderately reactive | stable bis(o-nitrophenyl)methyl ester | stable | stable | stable 9-anthrylmethyl ester | stable | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | stable piperonyl ester | stable | stable | stable trimethylsilyl ester | labile | labile | labile t-butyldimethylsilyl ester | labile | labile | moderately reactive S-t-butyl ester | stable | stable | stable 2-alkyl-1, 3-oxazolines | stable | stable | stable | pH 8.5-10 | pH 10-12 estermethyl | stable | moderately reactive methoxymethyl ester | stable | stable methylthiomethyl ester | stable | stable tetrahydropyranyl ester | stable | moderately reactive benzyloxymethyl ester | stable | stable phenacyl ester | stable | moderately reactive N-phthalimidomethyl ester | labile | labile 2, 2, 2-trichloroethyl ester | moderately reactive | labile 2-haloethyl ester | stable | labile 2-(p-toluenesulfonyl)ethyl ester | moderately reactive | labile t-butyl ester | stable | stable cinnamyl ester | stable | labile benzyl ester | stable | labile triphenylmethyl ester | stable | moderately reactive bis(o-nitrophenyl)methyl ester | stable | moderately reactive 9-anthrylmethyl ester | stable | stable 2-(9, 10-dioxo)anthrylmethyl ester | stable | moderately reactive piperonyl ester | stable | moderately reactive trimethylsilyl ester | labile | labile t-butyldimethylsilyl ester | labile | labile S-t-butyl ester | stable | stable 2-alkyl-1, 3-oxazolines | stable | stable | strong base | strong base (at 150 °C) estermethyl | labile | labile methoxymethyl ester | labile | labile methylthiomethyl ester | moderately reactive | labile tetrahydropyranyl ester | labile | labile benzyloxymethyl ester | labile | labile phenacyl ester | labile | labile N-phthalimidomethyl ester | labile | labile 2, 2, 2-trichloroethyl ester | labile | labile 2-haloethyl ester | labile | labile 2-(p-toluenesulfonyl)ethyl ester | labile | labile t-butyl ester | labile | labile cinnamyl ester | labile | labile benzyl ester | labile | labile triphenylmethyl ester | labile | labile bis(o-nitrophenyl)methyl ester | labile | labile 9-anthrylmethyl ester | labile | labile 2-(9, 10-dioxo)anthrylmethyl ester | labile | labile piperonyl ester | labile | labile trimethylsilyl ester | labile | labile t-butyldimethylsilyl ester | labile | labile S-t-butyl ester | moderately reactive | labile 2-alkyl-1, 3-oxazolines | moderately reactive | labile

Behavior under thermal conditions

 | 150 °C (degrees Celsius) | 250 °C (degrees Celsius) | 350 °C (degrees Celsius) estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | reactive methylthiomethyl ester | stable | stable | reactive tetrahydropyranyl ester | moderately reactive | labile | reactive benzyloxymethyl ester | stable | stable | reactive phenacyl ester | stable | stable | reactive N-phthalimidomethyl ester | stable | moderately reactive | reactive 2, 2, 2-trichloroethyl ester | moderately reactive | labile | reactive 2-haloethyl ester | stable | moderately reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | moderately reactive | labile | reactive t-butyl ester | moderately reactive | labile | labile cinnamyl ester | reactive | reactive | reactive benzyl ester | stable | stable | reactive triphenylmethyl ester | moderately reactive | labile | reactive bis(o-nitrophenyl)methyl ester | stable | stable | reactive 9-anthrylmethyl ester | stable | stable | reactive 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | reactive piperonyl ester | stable | stable | reactive trimethylsilyl ester | stable | stable | reactive t-butyldimethylsilyl ester | stable | stable | reactive S-t-butyl ester | moderately reactive | labile | reactive 2-alkyl-1, 3-oxazolines | stable | stable | reactive
| 150 °C (degrees Celsius) | 250 °C (degrees Celsius) | 350 °C (degrees Celsius) estermethyl | stable | stable | stable methoxymethyl ester | stable | stable | reactive methylthiomethyl ester | stable | stable | reactive tetrahydropyranyl ester | moderately reactive | labile | reactive benzyloxymethyl ester | stable | stable | reactive phenacyl ester | stable | stable | reactive N-phthalimidomethyl ester | stable | moderately reactive | reactive 2, 2, 2-trichloroethyl ester | moderately reactive | labile | reactive 2-haloethyl ester | stable | moderately reactive | reactive 2-(p-toluenesulfonyl)ethyl ester | moderately reactive | labile | reactive t-butyl ester | moderately reactive | labile | labile cinnamyl ester | reactive | reactive | reactive benzyl ester | stable | stable | reactive triphenylmethyl ester | moderately reactive | labile | reactive bis(o-nitrophenyl)methyl ester | stable | stable | reactive 9-anthrylmethyl ester | stable | stable | reactive 2-(9, 10-dioxo)anthrylmethyl ester | stable | stable | reactive piperonyl ester | stable | stable | reactive trimethylsilyl ester | stable | stable | reactive t-butyldimethylsilyl ester | stable | stable | reactive S-t-butyl ester | moderately reactive | labile | reactive 2-alkyl-1, 3-oxazolines | stable | stable | reactive