Sultenes, Sultines, and Sultones

Sultenes, Sultines, and Sultones.—Further reports have appeared on the formation of sultones from SO3 and dienes and from the cycloaddition of c-amino-methylene-ketones and sulphene. Unusual sultone formations occurred during the reaction of a ketose derivative with mesyl chloride and during the rearrangements of bicyclic ketones that were induced by sulphuric acid, respectively. The kinetics of reactions of sultones (181) with nucleophiles and the enthalpy changes accompanying their alkaline hydrolysis, which allow an estimation of differences in ring strain between the five- and six-membered sultones, have been studied. 

A further report on a [ r -1- tttt]-cycloaddition of a diene and SO2 has appeared the reaction of o-quinodimethane with SOj afforded mainly the cyclic sulphinate (182), and only small amounts of the [n -1- nn] product were formed. 

Yunker and B. Fraser-Reii J. Chem. Soc., Chem. Commun., 1978,325. 

Several sultams have been prepared by cycloaddition reactions similar to those applied to the synthesis of sultones. Thus, the generation of sulphene in the presence of pyridine gave the sultam (186). Activated dienes reacted with simple iV-sulphonylamines, e.g. MeN=S02, to give unsaturated sultams such as (187), and thione S-imides reacted smoothly as 1,3-dipoles to give cyclic sulphenamides (188), or as dienophiles, with the formation of A -dihydrothiopyran l-imides.  

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