Thietane 1,1-dioxides ring opening reactions

Treatment of cis- or tra 5-2,4-diphenyl thietane 1,1-dioxide with t-butoxy-magnesium bromide or ethylmagnesium bromide gives sultines (cyclic sulfin-ates) in which the stereochemistry is preserved (e.g., 171) and cyclo-propanesulfinic acids (e.g., 172). Bases such as hydroxide ion or triethyl-amine cause ring-opening of 3-amino substituted thietane sulfones via an elimination reaction as shown for The... 

For addition reactions that lead to ring-opening, see Section D. The use of addition reactions to synthesize thietane 1,1-dioxides has been discussed previously (Section V.3.C.). 

The thietane ring of the carboxylate derivative 352 is apparently opened by loss of carbon dioxide. possibly via a thiete intermediate. Isonitriles and ynamines effect ring-expansions of 2,4-bis(imino)thietanes, and similar reactions of enamines and ynamines with tris(imino)thietane, 353 have been reported. The nucleophiles — methanol, ethanethiol, and diethylamine — attack the a-carbon atom of 353, which bears the iminosulfonyl group, to give ring-opened products, for example, 353a. The reactions with sodium azide or hydrazoic acid take a different course. ... 

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