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Original Articles

Synthesis of some 4-(2′-hydroxyaryl)-5-ethyl-2-(N, N-dialkylamino)-1,3-dithiolium salts

Pages 155-162 | Received 26 Mar 2003, Accepted 12 May 2003, Published online: 08 Jun 2010
 

Abstract

The synthesis of 4-(2′-hydroxyaryl)-5-ethyl-2-(N,N-dialkylamino)-1,3-dithiolium salts (6a–e) has been accomplished by the heterocyclization of the corresponding carbodithioates (3a–e). The required starting materials (1a,b) have been prepared by regioselective bromination of 1-(2′-hydroxyaryl)butanones (4a,b). Under basic conditions, salts 6a–e afford anhydro-hydroxides 7a–e, which are mesoionic compounds with an intramolecular charge-transfer UV/Vis absorption where the donor moiety is linked through σ-bonded bridges (C5-S1, C4-S3) to the acceptor moiety.

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