Accession Number : AD0765523

Title :   New Chemistry of Hydrides.

Descriptive Note : Final rept. 1 Jul 72-30 Jun 73,

Corporate Author : PURDUE RESEARCH FOUNDATION LAFAYETTE IND

Personal Author(s) : Brown,Herbert C.

Report Date : JUL 1973

Pagination or Media Count : 22

Abstract : Lithium triethylborohydride has been established to be the most powerful simple nucleophile known for SN2 displacements. It reduces epoxides rapidly and quantitatively to their Markovnikov alcohols. Highly labile bicyclic epoxides are reduced without rearrangement. Aliphatic and aromatic carboxylic acids are selectively reduced rapidly and quantitatively to the corresponding alcohols by borane-THF in the presence of a variety of other functional groups such as ester, nitro, halogen, keto, cyano, etc. Potassium triisopropoxylborohydride in THF exhibits exceptionally mild reducing properties, yet rapidly reduces cyclic and bicyclic ketones with powerful steric control. Product analysis of the reaction of lithium triethylborohydride with representative organic functional groups has been carried out. (Author)

Descriptors :   (*BOROHYDRIDES, *REDUCTION(CHEMISTRY)), KETONES, DISPLACEMENT REACTIONS, LITHIUM COMPOUNDS, BORON COMPOUNDS, HYDRIDES, STEREOCHEMISTRY, HALOGENATED HYDROCARBONS, CARBOXYLIC ACIDS, CYCLOHEXANONES, NITRILES, ORGANIC COMPOUNDS, BORATES

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE