ELECTROCHEMICAL STUDIES ON HALOAMIDES .8. ELECTROSYNTHESIS OF N-(HALO)VINYLAMIDES

Citation
Ma. Casadei et al., ELECTROCHEMICAL STUDIES ON HALOAMIDES .8. ELECTROSYNTHESIS OF N-(HALO)VINYLAMIDES, Gazzetta chimica italiana, 123(8), 1993, pp. 457-462
Citations number
22
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
ISSN journal
0016-5603
Volume
123
Issue
8
Year of publication
1993
Pages
457 - 462
Database
ISI
SICI code
0016-5603(1993)123:8<457:ESOH.E>2.0.ZU;2-M
Abstract
The electrochemical reduction of N-haloethylamides 1a,b-4a,b (X=OCOCH3 , Cl)at a mercury pool cathode in HCON(CH3)2 (or CH3CN) - 0.1 mol dm-3 Et4NClO4 solution has been investigated. 2,2,2-trichloroethyl derivat ives la-4a (X=OCOCH3, Cl) give rise to the corresponding N-(2,2-dichlo rovinyl)amides 5a-8a in good to excellent yields, whereas in the case of N-(2,2-dichloroethyl)amides 1b-4b the course of the reduction depen ds on the nature of the substituent at N-C(alpha) and/or of the amide moiety. Acetamides lb (X=OCOCH3, Cl) yield a mixture of isomeric 5b, b ut pyrrolidone derivatives 2b behave differently depending on X. If X= Cl the expected isomeric dehydrohalogenation products 6b are formed, w hereas vinylpyrrolidone 6c, in addition to 6b, is formed from 2b, X=OC OCH3. High yields of 6c are attained by treatment of N-(2-chloroethyl) -2-pyrrolidone, 9, with the electrogenerated pyrrolidone anion.