Direct Dichlorovinylation of Some Carbonyl Compounds by Trichloroethylene Under Conditions of Phase-Transfer Catalysis

Andrzej Jończyk , Agnieszka H Gierczak

Abstract

Reaction of ketones 1 and 3 with trichloroethylene (TRI) carried out in the presence of 50\% aq. NaOH and TBAHS as a catalyst, in ethyl ether (phase-transfer catalysis, PTC) afford 1,2-dichlorovinylated ketones 2 and 4, respectively in good yields, usually as mixtures of Z and E isomers. PTC reaction of aldehydes 5 with TRI, carried out with DMSO instead of TBAHS, yields O-dichlorovinylated products 6, as mixtures of isomers in the case of 6a. These products are formed via C- or O-addition of ambident enolate anions to dichloroacetylene (generated from TRI by a base) and fast protonation of highly basic dichlorovinyl anions thus formed.
Author Andrzej Jończyk (FC)
Andrzej Jończyk,,
- Faculty of Chemistry
, Agnieszka H Gierczak
Agnieszka H Gierczak,,
-
Journal seriesTetrahedron, ISSN 0040-4020
Issue year2000
Vol56
No33
Pages6083-6087
Publication size in sheets0.5
Keywords in Englishaddition reactions, dichloroacetylene, enolates, phase-transfer
ASJC Classification1605 Organic Chemistry; 3002 Drug Discovery; 1303 Biochemistry
DOIDOI:10.1016/S0040-4020(00)00557-3
URL http://www.sciencedirect.com/science/article/pii/S0040402000005573
Languageen angielski
Score (nominal)30
Publication indicators Scopus SNIP (Source Normalised Impact per Paper): 2014 = 0.905; WoS Impact Factor: 2006 = 2.817 (2) - 2007=2.854 (5)
Citation count*5 (2013-01-30)
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