5337-26-8Relevant academic research and scientific papers
ELECTROCHEMICAL STUDIES ON HALOAMIDES. PART VIII. ELECTROSYNTHESIS OF N-(HALO)VINYLAMIDES
Casadei, Maria Antonietta,Cesa, Stefania,Moracci, Franco Micheletti,Inesi, Achille
, p. 457 - 462 (2007/10/02)
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 derivatives 1a-4a (X = OCOCH3, Cl) give rise to the corresponding N-(2,2-dichlorovinyl)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 depends on the nature of the substituent at N-Cα and/or of the amide moiety.Acetamides 1b (X = OCOCH3, Cl) yield a mixture isomeric 5b, but pyrrolidone derivatives 2b behave differently depending on X.If X = Cl the expected isomeric dehydrohalogenation products 6b are formed, whereas vinylpyrrolidone 6c, in addition to 6b, is formed from 2b, X = OCOCH3.High yields of 6c are attained by treatment of N-(2-chloroethyl)-2-pyrrolidone, 9, with the electrogenerated pyrrolidone anion.
