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Original Articles

CHLOROSULFONATION OF αβ-UNSATURATED ARYLIDENE KETONES

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Pages 135-142 | Received 27 Jul 1993, Accepted 26 Aug 1993, Published online: 23 Sep 2006
 

Abstract

2-Thienylideneacetone (4), and the benzylidene derivatives of ethyl methyl ketone (19) and diethyl ketone (20) were reacted with excess chlorosulfonic acid to give the thienylidene 5,β-disulfonyl chloride (5) and the styrene disulfonyl chlorides (21 and 22). These were characterized by preparation of the sulfonamides (6-9, 23 and 24) required for screening as pest control agents. Benzylidene acetone (1) was condensed with aryl aldehydes to give the corresponding 1,5-diaryl-1,4-dien-3-ones (25-28), but the condensation failed with p-anisaldehyde and o-vanillin. Attempted chlorosulfonation of compounds (25 and 28) was unsuccessful and the products could not be characterised as sulfonamide derivatives. The 1H NMR spectra of selected compounds are briefly discussed.

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