Sulfimidation

Sulfimides have been utilized extensively for the synthesis of monocyclic ring systems as well as ring annulations. 

The taste of saccharin was further studied, and it was found that (1) the alkaline-earth-metal salts are sweet, whereas the heavy-metal salts are astringent (2) the sweet taste is lost if the sulfimide ring is cleaved, or if... 

The synthesis of sulfoximides and sulfimides has attracted considerable attention in recent years due to the potential utility of these compounds as efficient auxiliaries and chiral ligands in asymmetric synthesis (reviews [86-88]). Transition metal-catalyzed nitrene transfer to sulfoxides and sulfides is an efficient and straightforward way to synthesize sulfoximides and sulfimides, respectively. Bach and coworkers reported the first iron-catalyzed imination of sulfur compounds with FeCl2 as catalyst and B0CN3 as nitrene source. Various sulfoxides and sulfides were... 

Similar results were reported independently by Shingaki and coworkers for the S, S-dimethyl-Af-ethoxycarbonyl sulfimide analogs. The photolysis of the higher valent sulfoximide derivatives, ArS02N=S(0)Me2, had earlier been reported by Abramovitch and Takaya ° not to yield the expected sulfonylnitrene but instead to give products arising... 

Moody and co-workers independently reported the synthesis of azathiabenzenes by thermolysis <86JCS(P1)483>. Azides 51a and 51b were decomposed in boiling toluene to give the corresponding cyclic sulfimides 52a and 52b in 52% and 13% yields, respectively (Scheme 14). 

The sulfimide group R2S = NR is isoelectronic with R2S = O, and recent studies have revealed the first examples of macrocyclic derivatives from reaction of the thia crown with MSFI.155,156 These compounds are of interest as ligands in their own right, and also because they provide a means of functionalizing the thiacrown at the S atom and hence the possibility of introducing pendant groups. 

Benzofuroxan, b43 Benzoglyoxaline, b39 Benzoic acid hydrazide, b71 Benzhydroxylamine, al59 o-Benzoic sulfimide, si... 

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