A CONJUGATE ADDITION SULFOXIDE ELIMINATION ROUTE TO ALLYLIC DIFLUOROPHOSPHONATES

Authors
BLADES K PERCY JM
Citation
K. Blades et Jm. Percy, A CONJUGATE ADDITION SULFOXIDE ELIMINATION ROUTE TO ALLYLIC DIFLUOROPHOSPHONATES, Tetrahedron letters, 39(49), 1998, pp. 9085-9088
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
49
Year of publication
1998
Pages
9085 - 9088
Database
ISI
SICI code
0040-4039(1998)39:49<9085:ACASER>2.0.ZU;2-Z
Abstract
Cerium-mediated conjugate additions of (diethoxyphosphinoyl) difluorom ethynithium to cyclic vinyl sulfoxides proceeded smoothly; thermal sul foxide elimination afforded the products of formal vinylation, attachi ng the difluoromethylenephosphonato group to an alkenyl carbon atom. W ith acyclic vinyl sulfoxides, the addition occurred in moderate to poo r yield. Addition failed completely in the absence of cerium(III) chlo ride, and was facilitated by an excess of the reagent. (C) 1998 Elsevi er Science Ltd. All rights reserved.