Reactions of aryl phenylacetates with secondary amines in MeCN. Structure-reactivity relationship in the ketene-forming eliminations and concurrent E2 and E1cb …

BR Cho, YK Kim, CO Maing Yoon

Index: Cho, Bong Rae; Kim, Yong Kwan; Yoon, Choon-Ock Maing Journal of the American Chemical Society, 1997 , vol. 119, # 4 p. 691 - 697

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Citation Number: 24

Abstract

Elimination reactions of aryl esters of arylacetic acids 1 and 2 promoted by R2NH in MeCN have been investigated kinetically. The reactions are second-order and exhibit β= 0.44- 0.84,| βlg|= 0.41-0.50, and ρH= 2.0-3.6. Brønsted β and| βlg| decrease with the electron- withdrawing ability of the β-aryl substituent. Hammett ρH values remain nearly the same, but the| βlg| value increases as the base strength becomes weaker. Both ρH and β decrease ...