Tetrahedron letters

Evidence of a stepwise acyl-transfer reaction mechanism: Nonlinear Hammett plots for reactions of p-nitrophenyl substituted benzoates with hydroxide and p- …

IH Um, EK Chung, DS Kwon

Index: Um, Ik-Hwan; Chung, Eun-Kyung; Kwon, Dong-Sook Tetrahedron Letters, 1997 , vol. 38, # 27 p. 4787 - 4790

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Citation Number: 20

Abstract

The Hammett plots obtained for the title reactions exhibit a break, ie ϱacyl values decrease from 2.21∼ 2.44 to 1.45∼ 1.52 as the acyl substituent becomes a strong electron withdrawing group (σ> 0.6). Such a break in the Hammett plots is suggestive of a change in the reaction mechanism and strong evidence of a stepwise mechanism for the acyl-transfer reaction.

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