Direct Dichlorovinylation of Some Carbonyl Compounds by Trichloroethylene Under Conditions of Phase-Transfer Catalysis
Andrzej Jończyk , Agnieszka H Gierczak
AbstractReaction 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.
|Journal series||Tetrahedron, ISSN 0040-4020|
|Publication size in sheets||0.5|
|Keywords in English||addition reactions, dichloroacetylene, enolates, phase-transfer|
|ASJC Classification||; ;|
|Publication indicators||: 2014 = 0.905; : 2006 = 2.817 (2) - 2007=2.854 (5)|
|Citation count*||5 (2013-01-30)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.