Imido sulfur compounds

Alkenes can be aminated in the allylic position by treatment with solutions of imido selenium compounds R—N—Se=N—R. The reaction, which is similar to the allylic oxidation of alkenes with Se02 (see 14-4), has been performed with R = t-Bu and R=Ts. The imido sulfur compound TsN=S=NTs has also been used... 

Imido selenium compounds Se(NR)2, where R = Bu or Ts, were first noted to give allylic amination of alkenes and alkynes.232 Formally the NR function is inserted into the allylic C—H bond yielding the C—NHR moiety. Related reactivity was also found for the sulfur imides, S(NR)2.233 Reactions between 1,3-dienes and Se(NTs)2 give [4 + 2] adducts which, in the presence of TsNH2, react to generate 1,2-disulfonamides.234... 

Imido chalcogen halides of the type RNEC12 (E=S, Se, Te) provide an interesting illustration of the reluctance of the heavier chalcogens to form -N=E< double bonds. The sulfur derivatives RNSX2 (X=F, Cl) are stable, monomeric compounds. 

Imido chlorides such as the oxathiazolines (179) behave typically, reacting with water to form cyclic imides, and with amines and sulfur nucleophiles to yield the expected derivatives (75MI43401). The chlorodithiazolone (77) is itself prepared by hydrolysis of the chlorodifluoro compound (180) (71CB2732). 

Compounds of these types are not covered in the I.U.C. rules. In substantial agreement with Chemical Abstracts usage many of these compounds can be named as amido ( —NH2), imido (/NH), and nitrido (instead of the more usual nitrilo for N) substitution derivatives of the oxygen acids (ammono- and ammonoaquophosphoric, -phosphorous, and -sulfuric acids) -J... 

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