GENERATION AND TRAPPING OF ALPHA,ALPHA'-DIOXOSULFINES FROM 1,4-OXATHIINE-S-OXIDES

Authors
CAPOZZI G FRATINI P MENICHETTI S NATIVI C
Citation
G. Capozzi et al., GENERATION AND TRAPPING OF ALPHA,ALPHA'-DIOXOSULFINES FROM 1,4-OXATHIINE-S-OXIDES, Tetrahedron letters, 36(28), 1995, pp. 5089-5092
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
28
Year of publication
1995
Pages
5089 - 5092
Database
ISI
SICI code
0040-4039(1995)36:28<5089:GATOAF>2.0.ZU;2-J
Abstract
The 1,4-oxathiine-S-oxides 6 when heated at 60 degrees C in CHCl3 unde rgo a retro Diels-Alder reaction with generation of alpha,alpha'-dioxo sulfine 8. This reactive intermediate can be trapped by electron rich dienophiles as well as by dienes. In both cases the cycloaddition reac tions show interesting stereoselective features.