Relative rates and stereochemistry of the iodomethylzinc iodide methylenation of some hydroxy-and methoxy-substituted cyclic olefins

JHH Chan, B Rickborn

Index: Chan,J.H.-H.; Rickborn,B. Journal of the American Chemical Society, 1968 , vol. 90, p. 6406 - 6411

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Citation Number: 75

Abstract

Abstract: Relative rates were determined for methylenation of the following compounds: 2- cyclohexenol (l), 1. OO; 2-cyclohexenyl methyl ether (2), 0.50; 1-cyclohexenylmethanol (3), 0.46; cis-5-methylcyclohexenol (4), 1.54; trans-5-methylcyclohexenol (5), 0.46; 3- cyclohexenol (6), 0.091; 1 methoxycyclohexene (7), 0.059. The reactions of 1, 4, 5, and 6 were shown to occur with high stereospecificity. In contrast, 3-cyclohexenylmethanol (8) ...