Organometallic reactions. Part XVIII. The reactions of N-sulphinyltoluene-p-sulphonamide and of N-(2,2,2-trichloroethylidene)toluene-p-sulphonamide with some tributyltin–oxygen and –nitrogen compounds

Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39700001570

Abstract

The sulphonyl group in the structures p-MeC6H4·SO2·N:CH·CCl3 and p-MeC6H4·SO2·N:S:O activates the adjacent N:S or N:C double bond, so that both these compounds react very readily with a variety of tributyltin–oxygen and –nitrogen compounds. The adducts of N-sulphinyltoluene-p-sulphonamide with bistributyltin oxide and hexabutyl-N-phenyldistannazane readily eliminate NN-bistributylstannyltoluene-p-sulphonamide, which will react with toluene-p-sulphonamide itself to give N-tributylstannyltoluene-p-sulphonamide. N-(2,2,2-Trichloroethylidene)toluene-p-sulphonamide has acceptor properties similar to, but rather weaker than, those of chloral.

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