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Cycloaddition of imines with allene. formation mechanism of azetidine ring

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
36
Issue
44
Identifiers
DOI: 10.1016/0040-4039(95)01700-r

Abstract

Abstract PM3 calculations of possible pathways for azetidine-ring formation reaction of imine with allene was performed, indicating that the reaction proceeds via a nonconcerted two-step mechanism in which the allene attacks toward the lone pair of nitrogen atom of imine moiety. Isolation of two stereoisomeric 2:1 cycloadducts from the reaction of 3,3-dimelhyl-3H-indole with phenylsulfonyl propadiene strongly supports the presence of a zwitterionic reaction intermediate.

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