ORGANOBORON COMPOUNDS. CDIV. A HYDRIDE TRANSFER REACTION IN THE SERIES OF ATE COMPLEXES OF 7-SUBSTITUTED 3-ALKYL-3-BORABICYCLONONANES AND 3-ALKYL-3-BORABICYCLONON-6-ENES

Article abstract of DOI:10.1016/0022-328X(83)80192-2

The ate complexes of 7-substituted 3-alkyl-3-borabicyclo<3.3.1>nonanes and of 3-alkyl-3-borabicyclo<3.3.1>non-6-enes react with acetyl chloride under mild conditions by an intermolecular β-hydride transfer mechanism to form 5-substituted 3-methylenedyclohex-1-ylmethyl(dialkyl)boranes.The latter compounds were converted, by oxidation with alkaline hydrogen peroxide, to 3-substituted 1-methylene-5-hydroxymethylcyclohexanes.The reaction of cycloalkylmethyl(dialkyl)boranes with aromatic aldehydes was applied to the synthesis of 1,3-di- and 1,3,5-tri-methylene derivatives of the cyclohexane series.