Tetrahedron

Reactions of 1-halocyclohexenes and methyl substituted 1-halocyclohexenes with potassium t-butoxide

AT Bottini, FP Corson, R Fitzgerald, KA Frost

Index: Bottini,A.T. et al. Tetrahedron, 1972 , vol. 28, p. 4883 - 4904

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Citation Number: 36

Abstract

Reactions of 1-halocyclohexenes and 1-halo-4-methylcyclohexenes with potassium t- butoxide (t-BuOK) in dimethyl sulfoxide and tetrahydrofuran have been shown to take place by three competing dehydrohalogenation mechanisms. These are: dehydrohalogenation across the C1 C6 bond to give a cyclohexyne; dehydrohalogenation across the C1 C6 bond to give a 1, 2-cyclohexadiene: and prototropic rearrangement to the corresponding 3 ...