THE REACTION OF N-PHENYLSULFONIMIDOYL CHLORIDE WITH TRIMETHYLSILYLETHENE - A NEW ROUTE TO 2-ALKENYLANILINES

Authors
HARMATA M KAHRAMAN M JONES DE PAVRI N WEATHERWAX SE
Citation
M. Harmata et al., THE REACTION OF N-PHENYLSULFONIMIDOYL CHLORIDE WITH TRIMETHYLSILYLETHENE - A NEW ROUTE TO 2-ALKENYLANILINES, Tetrahedron, 54(34), 1998, pp. 9995-10006
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
34
Year of publication
1998
Pages
9995 - 10006
Database
ISI
SICI code
0040-4020(1998)54:34<9995:TRONCW>2.0.ZU;2-B
Abstract
N-Phenylsulfonimidoyl chloride reads with trimethylsilylethene in the presence of aluminum chloride to give two product benzothiazines, one of which has been desilylated. The silylated benzothiazine can be depr otonated and alkylated, sometimes with very high diastercocontrol. Upo n treatment with fluoride, these silylated benzothiazines undergo desi lylation with concomitant cleavage of the carbon-sulfur bond to give 2 -alkenylsuifinanilides which can be hydrolyzed to the corresponding an ilines. (C) 1998 Elsevier Science Ltd. All rights reserved.