ENOLIC RADICAL DERIVED FROM ACETIC-ACID - A USEFUL RADICAL ALTERNATIVE TO ACETATE ENOLATE IN MICHAEL-TYPE REACTIONS

Authors
FOUBELO F LLORET F YUS M
Citation
F. Foubelo et al., ENOLIC RADICAL DERIVED FROM ACETIC-ACID - A USEFUL RADICAL ALTERNATIVE TO ACETATE ENOLATE IN MICHAEL-TYPE REACTIONS, Tetrahedron, 49(37), 1993, pp. 8465-8470
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
37
Year of publication
1993
Pages
8465 - 8470
Database
ISI
SICI code
0040-4020(1993)49:37<8465:ERDFA->2.0.ZU;2-Z
Abstract
The reaction of iodoacetic acid 1 with tributyltin chloride and sodium borohydride in the presence of different electrophilic olefins 2 (met hyl, allyl or tert-butyl acrylates, N,N-dimethyl or N,N-di-iso-propyl acrylamides, acrylonitrile, methyl methacrylate, methacrylonitrile and 1,1-dichloroethylene) and AIBN as an initiator yields, after treatmen t with aqueous sodium fluoride, the corresponding products 3 through a radical Michael-type process.