Tetrahedron

The effect of aryl substituents on arylcarbene reactivity

H Tomioka, K Tabayashi, Y Ozaki, Y Izawa

Index: Tomioka, Hideo; Tabayashi, Kazuo; Ozaki, Yasuji; Izawa, Yasuji Tetrahedron, 1985 , vol. 41, # 8 p. 1435 - 1440

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Citation Number: 13

Abstract

Substituted (p-MeO, p-Me, H, p-Cl, p-Br, m-Br, m-MeO, 3, 4-Cl2, p-CO2Me, m-CN and p-CN) monophenylcarbenes are generated in a binary mixture of substrates (methanol, cis-4- methyl-2-pentene and cyclohexane) and the relative rate of O—H insertion into methanol to stereospecific cyclopropanation of the olefin to C—H insertion into cyclohexane are calculated from the ratios of products and substrates. It is found (i) that the reactivities of ...