Conformational analysis of 2-substituted methylenecyclohexanes and 3-substituted cyclohexenes and the anomeric effect

Abstract
The analysis of the 13C and 1H nuclear magnetic resonance data of 2-substituted methylenecyclohexanes and 3-substituted cyclohexenes demonstrates that a double bond stabilizes the axial conformer for an electronegative substituent. Introduction of a methoxy group on the double bond further increases the relative stability of the axial conformer. These results are interpreted in terms of the 'double bond – no bond' resonance.

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