CYCLIZATION OF 6-BROMO-1,2-EPOXYHEXANE PROMOTED BY METAL-HALOGEN EXCHANGE: UNEXPECTED REGIOSELECTIVITY

Article abstract of DOI:10.1016/S0040-4039(01)81428-3

Treatment of 6-bromo-l,2-epoxyhexane (1) with one equivalent of sec-butyllithium afforded a 95:5 mixture of cyclopentylmethanol (4): cyclohexanol in approximately 40percent yield.An analogous tandem metal-halogen exchange/cycloalkylation process using the oxirane derivative (2) of 6-iodo-1-hexene gave virtually the same mixture of alcohols in >60percent yield.