Journal of the American Chemical Society

4-Oxazoline route to stabilized azomethine ylides. Controlled reduction of oxazolium salts

E Vedejs, JW Grissom

Index: Vedejs,E.; Grissom,J.W. Journal of the American Chemical Society, 1988 , vol. 110, p. 3238

Full Text: HTML

Citation Number: 59

Abstract

Abstract: Treatment of oxazolium salts with phenylsilane/CsF generates 4-oxazolines 14 in situ. Provided that R,= H or alkoxy, ring opening to azomethine ylides 15 occurs spontaneously and [2+ 31 cycloadducts are obtained in the presence of acrylate, N- phenylmaleimide, propiolate, or dimethyl acetylenedicarboxylate (DMAD) dipolarophiles. If R,= alkyl or aryl, the initially formed 4-oxazoline resists ring opening, probably due to ...