The Journal of Organic Chemistry

Conformational aspects of the directive effect of the homoallylic hydroxyl group in the Simmons-Smith reaction

JA Staroscik, B Rickborn

Index: Staroscik,J.A.; Rickborn,B. Journal of Organic Chemistry, 1972 , vol. 37, p. 738 - 740

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Citation Number: 38

Abstract

A series of substituted 3-cyclohexenols was prepared and subjected to the iodomethylzinc iodide methylenation reaction. Competitive kinetics establish that, in contrast to the allylic 2- cyclohexenols, the homoallylic 3-cyclohexenols react through the axial hydroxyl conformer. The compounds examined (!-%, I) are 3-cyclohexenol (l, O), cis-6-methyl-3-cyclohexenol (5.2), 1-methyl-3-cyclohexenol (4.0), trans-6-methyl-3-cyclohexenol (2.6), trans-1, 4, 5, 6, 7 ...