Jh. Choi et al., REDUCTION OF REPRESENTATIVE ORGANIC FUNCTIONAL-GROUPS WITH GALLANE-TRIMETHYLAMINE, Bulletin of the Korean Chemical Society, 18(3), 1997, pp. 274-280
The rates and stoichiometry of the reaction of gallane-trimethylamine
with selected organic compounds containing representative functional g
roups were examined in tetrahydrofuran solution under standardized con
ditions (THF, 0 degrees C). And its reducing characteristics were comp
ared with those of aluminum hydridetriethylamine(AHTEA). The rate of h
ydrogen evolution from active hydrogen compounds varied considerably w
ith the nature of the functional group and the structure of the hydroc
arbon moiety. Alcohols, phenol, amines, thiols evolved hydrogen rapidl
y and quantitatively. Aldehydes and ketones were reduced moderately to
the corresponding alcohols. Cinnamaldehyde was reduced to cinnamyl al
cohol, which means that the conjugated double bond was not attacked by
gallane-trimethylamine. Carboxylic acids, esters, and lactones were s
table to the reagent under standard conditions. Acid chlorides also we
re rapidly reduced to the corresponding alcohols. Epoxides and halides
were inert to the reagent. Caproamide and nitrile were stable to the
reagent, whereas benzamide was rapidly reduced to benzylamine. Nitropr
opane, nitrobenzene and azoxybenzene were stable to the reagent, where
as azobenzene was reduced to 1,2-diphenylhydrazine. Grimes and pyridin
e N-oxide were reduced rapidly. Di-n-butyl disulfide and dimethylsulfo
xide were reduced only slowly, but diphenyl disulfide was reduced rapi
dly. Finally, sulfones and sulfonic acids were inert to the reagent un
der the reaction.