Toluenesulfonyl group arylation

Aziridines can be prepared directly from double-bond compounds by photolysis or thermolysis of a mixture of the substrate and an azide. The reaction has been carried out with R = aryl, cyano, EtOOC, and RSO2, as well as other groups. The reaction can take place by at least two pathways. In one, the azide is converted to a nitrene, which adds to the double bond in a manner analogous to that of carbene addition (15-62). Reaction of NsONHC02Et/ CuO [Ns = A(/7-toluenesulfonyl-inimo)] and a conjugated ketone, for example, leads to the A-carboethoxy aziridine derivative.Calcium oxide has also been used to generate the nitrene.Other specialized reagents have also been used." ... 

Abbreviations are often used for monovalent groups that commonly appear in organic compounds. Some of these abbreviations are shown in Table 1.1. Aryl may be phenyl, a substituted phenyl, or a heteroaromatic group like furyl, pyridyl, or pyrrolyl. Tosyl is shorthand for p-toluenesulfonyl, mesyl is shorthand for methanesul louyi, and triflyl is shorthand for trifluoromethanesulfonvl. TsO, MsO-, and TI O are abbreviations for the common leaving groups tosylate, mesylate, and triflate, respectively. 

Acylation of the amino group at the 4-position of 3,4,5-triaminothiadia-zine 10b with trifluoroacetic acid, and with acetyl, benzoyl, caproyl, and p-toluenesulfonyl chloride, has been described (86FES862). The 4-aryl-diazonium salts have also been prepared (77JHC427), Reactions of 4,5-diaminothiadiazines are described with regard to the preparation of fused systems in Section II,C,2,a. 

Indole and its derivatives may be considered as enamines. Their reaction products with azides demonstrate, however, that in most cases complex dediazoniation products are formed rather than diazoalkanes. Their structure was elucidated mainly by Bailey s group (review Peach and Bailey, 1979). Under phase transfer conditions 2-aryl- or 2-heteroaryl-substituted indoles are converted into the corresponding 3-diazo-3//-indoles by 4-toluenesulfonyl azide (2-70) (Gonzalez and Galvez, 1981). 

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