Synthesis of Methylenecycloalkanes from Cycloalkenes via Borane Chemistry

Article abstract of DOI:10.1021/jo00316a038

B-(Cycloalkylmethyl)-9-BBN derivates, now readily available through the homologation reaction, are convenient substrates for the synthesis of exocyclic methylene compounds.The method appears to be general.Moreover, since the synthesis proceeds from the cycloalkene, it provides a valuable alternative to the customary methylenation of carbonyl compounds by the Wittig and related procedures.The method also provides a clean synthesis of deuterium-labeled compounds without positional scrambling or loss of label.