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Communication | Regular issue | Vol 41, No. 5, 1995, pp.883-888
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7026
A Possible Explanation for Preferential Stabilization of the Substituent Axial Conformation in Alkoxy- or Siloxy-substituted Six-membered Cyclic Compounds by the σ → σ* Orbital Overlap: Remarkable Effect of Electron-withdrawing Groups

Yoshimitsu Nagao* and Michimasa Goto

*Faculty of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770, Japan

Abstract

The substituent axial conformation in alkoxy- or siloxy-substituted six-membered cyclic compounds must be stabilized by the existence of an electronwithdrawing group or a double bond in their molecules, which can be rationalized in terms of the σ(C-H)→σ*(C-OR) or π(C=C)→σ*(C-OR) orbital overlap concept. The basicity of the oxygen atom of alkoxy and siloxy substituent groups may effect the relative stability of the substituent axial conformer.