Elimination reactions of N-alkyl-N-chlorothenylamines promoted by MeONa-MeOH and Et2NH-MeCN. Effect of the β-Aryl group on the imine-forming transition state

SY Pyun, DC Lee, YJ Seung…

Index: Pyun, Sang Yong; Lee, Dong Choon; Seung, Yoon Je; Cho, Bong Rae Journal of Organic Chemistry, 2005 , vol. 70, # 13 p. 5327 - 5330

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Citation Number: 8

Abstract

Elimination reactions of N-alkyl-N-chlorothenylamines 1-4 with MeONa-MeOH and Et2NH- MeCN have been studied kinetically. The elimination reactions are regiospecific, producing only the conjugated imines. The reactions are second order and exhibit substantial values of Hammett ρ and k H/k D, and an E2 mechanism is evident. The relative rates of elimination for Me/Et/i-Pr/t-Bu substituents are 1/0.5/0.2/0.02 with MeONa-MeOH and 1/0.4/0.2/0.06 ...