OLIGOMER FORMATION VIA REACTIONS OF 3-ETHYL-1-AZABICYCLO[1.1.0]BUTANEWITH ARENESULFONYL AZIDES

Authors
MARCHAND AP ALIHODZIC S
Citation
Ap. Marchand et S. Alihodzic, OLIGOMER FORMATION VIA REACTIONS OF 3-ETHYL-1-AZABICYCLO[1.1.0]BUTANEWITH ARENESULFONYL AZIDES, Tetrahedron, 54(50), 1998, pp. 15127-15136
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
50
Year of publication
1998
Pages
15127 - 15136
Database
ISI
SICI code
0040-4020(1998)54:50<15127:OFVRO3>2.0.ZU;2-K
Abstract
Electrophilic additions of arenesulfonyl azides (i.e., TsN3 and NsN(3) ) to 3-ethyl-1-azabicyclo[1.1.0]butane (1) in CDCl3 at 80 degrees C ha s been observed to result in the formation of oligomeric products. The mechanism of these reactions probably involves the formation of a car bocationic intermediate, i.e., N-arenesulfonyl-3-ethyl-3-azetidinyl ca rbocation, which subsequently can be trapped in situ either by :N-3(-) or by 1 to afford the observed reaction products. (C) 1998 Elsevier S cience Ltd. All rights reserved.