The Journal of Organic Chemistry

Stereoselectivity in the formation of heterocyclic amine oxides

Y Shvo, ED Kaufman

Index: Shvo, Youval; Kaufman, Edward D. Journal of Organic Chemistry, 1981 , vol. 46, # 10 p. 2148 - 2152

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Citation Number: 14

Abstract

The stereoselectivity of the oxidation of N-alkylpiperidines was studied with the aid of the conformationally biassing 4-tert-butyl substituent. The stereoselectivity was always 795% and showed little sensitivity to the nature of the N-alkyl substituent. The axial approach was found to be the predominating stereochemical oxidation path. A brief study of the effects of solvent, temperature, and oxidant on the stereoselectivity was made. The 1, 4- ...