The formation and structure determination of both acyclic and cyclic products in the reaction of sulfene and pyridines

Abstract

Sulfene, generated from methanesulfonyl chloride and triethylamine in acetonitrile reacts with itself to form a tetramer which may be isolated as an acyclic crystalline pyridinium sulfonate salt, 1. When sulfene is generated in tetrahydrofuran in the presence of pyridine, the 1,1,3,3-tetraoxide of 4,4a-dihydropyrido[1,2-d][1,5,2]dithiazine, 11, is formed. Structural evidence (including nmr and mass spectra) for these compounds, for homologs of 11, and for a series of acyclic polysulfonyl compounds derived from 1 is presented. An X-ray crystal structure determination was carried out on 9, the 5,7-dimethyl homolog of 11.