CHLOROSULFONATION OF ALPHA,BETA-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,beta-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 H-1 NMR spectra of selected compounds are briefly discussed.