Reactions of N-(chlorobenzyl) alkylamines with sodium methoxide in methanol. Steric effects in elimination reactions

BR Cho, JH Maeng, JC Yoon…

Index: Cho, Bong Rae; Maeng, Jun Ho; Yoon, Jong Chan; Kim, Tae Rin Journal of Organic Chemistry, 1987 , vol. 52, # 21 p. 4752 - 4756

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Citation Number: 7

Abstract

Reactions of N-chlorobenzylalkylamines in which the alkyl group is Me, Et, i-Pr, t-Bu, and sec-Bu with MeONa-MeOH have been investigated kinetically. The eliminations are quantitative and regiospecific, producing only benzylidenealkyhmines. The reactions are first order in base and first order in substrate, and an E2 mechanism is evident. The relative rates of elimination at 25 OC are 1/0.5/0.3/0.2/0.01 for Me/Et/i-Prlsec-Bu/t-Bu alkyl ...

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