MULTISTEP NUCLEOPHILIC-SUBSTITUTION OF THE HALOGEN ATOM IN 2-HALO-2-ALKENALS

Authors
RULEV AY ZINCHENKO SV KEIKO NA VORONKOV MG
Citation
Ay. Rulev et al., MULTISTEP NUCLEOPHILIC-SUBSTITUTION OF THE HALOGEN ATOM IN 2-HALO-2-ALKENALS, Russian chemical bulletin, 45(1), 1996, pp. 129-132
Citations number
18
Categorie Soggetti
Chemistry
Journal title
Russian chemical bulletin → ACNP
ISSN journal
10665285
Volume
45
Issue
1
Year of publication
1996
Pages
129 - 132
Database
ISI
SICI code
1066-5285(1996)45:1<129:MNOTHA>2.0.ZU;2-Q
Abstract
ipso-Substitution of the halogen atom in 2-halo-2-alkenals under the a ction of secondary amines proceeds via three consecutive steps: additi on, nucleophilic substitution, and beta-elimination (the Ad(N)-S-N-E m echanism). The main intermediates arising in the reactions of 2-chloro propenal and 2-chloro-2-butenal with piperidine were detected by NMR s pectroscopy. A general scheme of the reaction is proposed.