New Chemistry of Hydrides.
Final rept. 1 Jul 72-30 Jun 73,
PURDUE RESEARCH FOUNDATION LAFAYETTE IND
Pagination or Media Count:
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
- Organic Chemistry