Input interpretation
benzylidene acetal | behavior | stable
Reducing agents
lithium tri-tert-butoxyaluminum hydride LiAlH[OC(CH_3)_3]_3 | aluminium amalgam Al(Hg) | diisobutylaluminum hydride [(CH_3)_2CHCH_2]_2AlH | disiamylborane C_10H_23B_1 | lithium aluminum hydride LiAlH_4 | L-selectride Li[CH(CH_3)CH_2CH_3]_3BH | sodium borohydride NaBH_4 | zinc borohydride H_8B_2Zn_1 | hydrogen/rhodium H_2/Rh | stannous chloride/pyridine SnCl_2/C_5H_5N | diborane B_2H_6 (at 0 °C)
Oxidizing agents
iodine I_2 | osmium tetroxide OsO_4 | chromium trioxide/pyridine CrO_3/C_5H_5N | manganese dioxide/methylene chloride MnO_2/CH_2Cl_2 | selenium dioxide/pyridine SeO_2/C_5H_5N | quinone R(C=O)_n | singlet oxygen ^1O_2 | dimethyl sulfoxide (CH_3)_2SO (at 100 °C) | hydrogen peroxide H_2O_2 (pH 10-12) | potassium hexacyanoferrate(III) K_3Fe(CN)_6 (pH 8) | sodium hypochlorite NaOCl (pH 10) | sodium periodate NaIO_4 (pH 5-6) | peroxycarboxylic acid RCO_3H (at 0 °C) | lead(IV) cation Pb^(4+) (at 25 °C)
Electrophilic agents
acid chloride RCOCl
Nucleophilic agents
sodium methoxide NaOCH_3 | enolate (RCOCR_2)^- | organocopper R_2CuLi | organolithium RLi | ammonia NH_3 | primary amine RNH_2 | sodium cyanide NaCN (pH 12)
Organometallic agents
organozinc R_2Zn | organocopper R_2CuLi | organolithium RLi
Basic agents
dimsyl sodium C_2H_5ONaS | lithium diisopropylamide [(CH_3)_2CH]_2NLi | potassium tert-butoxide (CH_3)_3COK | sodium amide NaNH_2 | sodium hydride NaH | triphenylmethyl sodium C_19H_15Na_1 | pyridine C_5H_5N | tertiary amine NR_3
Acidic agents
copper(II) cation/pyridine Cu^(2+)/C_5H_5N | lithium perchlorate/magnesium bromide LiClO_4/MgBr_2 | tosic acid C_7H_8O_3S (at 0 °C)