SOME REDUCING AGENTS IN ORGANIC CHEMISTRY

alkene H2/Pt or H2/Pd H2/Pt/BaSO4 LiAlH4 LiAl(OtBu)3H NaBH4 B2H6, BH3 Na or Li Na, NH3 Sn,Zn,orFe,HCl Zn(Hg),HCl Mg RMgX RLi, RNa R2CuLi, R2Cd O=C !C! RC/C! 3P=CHR NH2NH2, OH! alkene alkyne aromatic alkyl ring halide
! no reaction

alkyne + +

aromatic alkyl ring halide high P

alcohol OH

epoxide +

aldehyde ketone + ! + ! + slow + +

acid chloride + + + + + !

carbox. acid !

ester +

amide +

nitrile +

nitro, nitroso +

! ! ! +

CH ! ! + CH + + +

OH

+ !

+ slow + +

+ ! OH +

+ + ! +

+ ! some +

+ ! ! +

+ ! ! !

+ +

+ + + + + + + +

CH CH

+ + + + +

OH OH

+ + slow

+ + slow + CH + +

OH OH

+ OH CH OH OH hydrol acid chloride OH carbox. acid ester amide nitrile NO2 NO + ?

OH OH OH

+ +

+ CH + +

alcohol

epoxide

aldehyde ketone

+ reduction of functional group

CH, OH acid-base reaction

? expect reaction but no evidence found

Alkenes conjugated with carbonyls may be reduced by hydride and organometallic reagents, unlike nonpolar alkenes; C=O/C=C selectivity is always sensitive to stereochemistry A blank space means that information was not readily available or provided examples of both + and !; contributions welcome. L. M. SWEETING 1995