Thietane sulfilimines

Four-Membered Sulfur Heterocydes TABLE 7. THIETANE SULFILIMINES AND 5-AMINO SALTS... 

O-Mesitylenesulfonylhydroxylamine (MSH) reacts with thietane to give the 5-amino salt 81. " An attempt to prepare a sulfilimine by treatment of 81 with a basic ion exchange resin was not successful.Chloramine-T gives the N-(p-tolylsulfonyl)sulfilimine 82. Several substituted thietanes yield the A -tosyl-sulfilimines in 56-100% yields. ... 

The reaction of sulfides, such as thietane with chloramine-T previously mentioned, proceeds by initial formation of a sulfur-chlorine bond. The intermediate sulfonium salt may yield the sulfilimine or the sulfoxide ... 

Treatment of thietanes with chloramine T gives N-tosylsulfilimines, for example, 126. Acyclic and five-, six-, and seven-membered cyclic sulfides all react more rapidly than thietane. The mechanism has been investigated. The IR stretching vibrations of the S-N-SO2 system are at 948 and 759 cm", and the nmr spectrum of 3,3-dimethylthietane 1-tosylsulfilimine in benzene and chloroform suggests an equatorial conformation for the sulfilimine. Oxidation of this sulfilimine gives the sulfoximine derivative, 127. The two diastereomeric tosyl-sulfilimines of 3-methyl-3-phenylthietane complex at nitrogen with silver ion. ... 

Attempts to prepare the tosyl derivative of the sulfilimine 198 from the 5-amino salt 81 resulted in cleavage of the S-N bond to give ammonia and thietane. ... 

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