CHLOROSULFONATION OF αβ-UNSATURATED ARYLIDENE KETONES

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 pre...

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Veröffentlicht in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 1993-11, Vol.84 (1-4), p.135-142
Hauptverfasser: Cremlyn, Richard J., Bassin, Jatinder P., Graham, Steven, Saunders, David
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Sprache:eng
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Zusammenfassung: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 1 H NMR spectra of selected compounds are briefly discussed.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426509308034324