Mechanistic considerations for the consecutive cyclization of 2, 3-dibromopropylamine hydrobromide giving a strained molecule, 1-azabicyclo [1.1. 0] butane

K Hayashi, Y Ikee, S Goto, M Shiro…

Index: Hayashi, Kazuhiko; Ikee, Yoshifumi; Goto, Satoru; Shiro, Motoo; Nagao, Yoshimitsu Chemical and Pharmaceutical Bulletin, 2004 , vol. 52, # 1 p. 89 - 94

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Citation Number: 10

Abstract

The effective formation of 1-azabicyclo [1.1. 0] butane (2) by treatment of 2, 3- dibromopropylamine hydrobromide (1) with n-BuLi could be understood considering a rational reaction pathway via both transition states 10 and 19 based on the intramolecular Br··· Li+ coordination. A similar cyclization pathway starting from N-benzyl-3- bromopropylamine hydrochloride (17) to afford N-benzylazetidine (18) could also be ...

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