Abstract
A systematic analysis of the X-ray structures of cyclohexanes, cylcopentanes and open-chain compounds containing gem.-dimethyl groups has revealed that a static scissor-type deformation at the quaternary C atom is absent. Unexpectedly the CCC bond angles in α-position to the quaternary C atom are significantly larger than the standard values in the unsubstituted reference structures. This distortion is interpreted in terms of gauche interactions. Based on the presently available data for structures containing gem.-dimethyl groups, the structure-reactivity relationship observed by Thorpe and Ingold for this class of compounds, has an origin different from static scissor-like distortions at the quaternary C atom.
Published Version
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