Tetrahedron

The stereochemistry and reactivity of unsaturated compounds—III: Reactivity of the double bond in Δ30cyclohexene and Δ4-octalin derivatives relative to their …

GP Kugatova-Shemyakina, GM Nikolaev, VM Andreev

Index: Kugatova-Shemyakina,G.P. et al. Tetrahedron, 1967 , vol. 23, p. 2721 - 2733

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Citation Number: 12

Abstract

A study of the double bond reactivity in Δ3-cyclohexene derivatives with one polar substituent in the side chain and Me substituents in the ring has shown that the preferred conformation for these compounds, indepenent of their stereochemistry, has the polar group axial, giving rise to supra-annular interaction. Such interaction decreases the nucleophilicity of the ring double bond. A similar study of Δ4-octalin-1, 2-dicarboxylic acids and their ...