Synthesis of Azetidine and Pyrrolidine Derivatives through Selenium??Induced Cyclization of Secondary Homoallylamines− A 77Se NMR Study

X Pannecoucke, F Outurquin…

Index: Pannecoucke, Xavier; Outurquin, Francis; Paulmier, Claude European Journal of Organic Chemistry, 2002 , # 6 p. 995 - 1006

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Citation Number: 16

Abstract

Abstract Treatment of α-alkyl and α, α-dialkyl homoallylic amines 1 with PhSeX (X= Cl, Br, I), in CH 3 CN containing sodium carbonate produced mixtures of azetidines 2 and pyrrolidines 3. The cyclization also occurred in the absence of Na 2 CO 3, and the corresponding azetidinium and pyrrolidinium salts 2 (HX) and 3 (HX) were formed in CDCl 3 or CH 3 CN. The crude reaction mixtures were analysed by 77 Se NMR. Each product− 2, 3, 2 (HX), ...