Organoboranes for synthesis. 13. Simple, efficient syntheses of long-chain alcohols and carboxylic acids

Article abstract of DOI:10.1016/S0040-4020(01)85609-X

General, convenient and simple syntheses of long straight chain alcohols and carboxylic acids were developed utilizing organoborane chemistry. One of the methods entails the thermal isomerization of long-chain alkyldicyclohexylboranes, followed by oxidation. An alternative procedure for the preparation of long-chain alcohols involves the KAPA isomerization of internal alkynes to the terminal derivative, followed by dihydroboration with 9-BBN and oxidation. Alternatively, the terminal alkyne can be oxidised directly to the carboxylic acid. In another strategy, the C₃₀-alcohol triaxontanol was prepared by employing high pressure carbonylation of a borane intermediate.