STEREOSPECIFIC CROSS-COUPLING REACTIONS OF 3-ARYLSULFINYLPROPENOATES WITH ORGANOMETALLIC REAGENTS

Citation
C. Cardellicchio et al., STEREOSPECIFIC CROSS-COUPLING REACTIONS OF 3-ARYLSULFINYLPROPENOATES WITH ORGANOMETALLIC REAGENTS, Gazzetta chimica italiana, 126(8), 1996, pp. 555-558
Citations number
44
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
ISSN journal
0016-5603
Volume
126
Issue
8
Year of publication
1996
Pages
555 - 558
Database
ISI
SICI code
0016-5603(1996)126:8<555:SCRO3W>2.0.ZU;2-6
Abstract
(E)- or (Z)-3-arylsulfinylpropenoates have been reacted with several o rganometallic rea gents. Grignard reagents were found to promote only the complete substitution of the arylsulfinyl group in good yields up to 92%. The reaction followed a stereochemical course of retention of configuration with high values of stereospecificity (up to 99%) in mos t cases. The observations made are discussed in the light of current v iews concerning nucleophilic substitution at a vinyl carbon atom. The addition-elimination pathway is considered valid, whereas a route invo lving the formation of a sulfurane as an intermediate, followed by a l igand coupling, is considered less likely.