Journal of the American Chemical Society

Tosylate oxygen scrambling associated with ion-pair return in the threo-3-p-anisyl-2-butyl system

HL Goering, BE Jones

Index: Goering, Harlan L.; Jones, Barry E. Journal of the American Chemical Society, 1980 , vol. 102, # 5 p. 1628 - 1633

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Citation Number: 17

Abstract

Abstract: Ion-pair return involved in acetolysis of threo-3-p-anisyl-2-butyl p-toluenesulfonate (6-OTs) results in racemization of optically active 6-OTs (krac) and equilibration of the sulfonate oxygen atoms of'* O-labeled 6-OTs (keq). In this system external ion-pair return is involved, Presumably most, if not all, external ion-pair return is eliminated by 0.03 M LiC104. The oxygen equilibration to racemization (total measurable return) ratio for internal return,( ...

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