Tetrahedron

Experimental evidence for AcO-7 neighboring group participation

SH Wilen, L Delguzzo, R Saferstein

Index: Wilen, Samuel H.; Delguzzo, Luciano; Saferstein, Richard Tetrahedron, 1987 , vol. 43, # 21 p. 5089 - 5094

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Citation Number: 20

Abstract

The reaction of diol diacetates with anhydrous aluminium chloride at ca 100° leads to displacement of only one of the acetoxy groups by chlorine. An oxygen-18 label study has shown that these displacements take place via acetoxonium intermediates and has provided direct evidence for the intervention of a seven-membered ring acetoxonium ion in the displacement of acetate by chlorine in 1, 4-butanediol diacetate.