Reaction with sulfonyl halides

Reaction with Sulfonyl Halides. Arylsulfonyl halides undergo reductive dimerization to form the corresponding disulfides (eq 35). Alkylsulfonyl halides, however, undergo this process under somewhat more vigorous conditions. Although sulfones generally do not react with TMS-I, certain cyclic sulfones are cleaved in a manner analogous to lactones. ... 

Table 6 gives a selection of reactions of sulfonyl halides with different unsaturated systems. 

Closely related is the reaction of tertiary amines with sulfonyl halides that contain an a hydrogen. In this case, the initial product is the highly reactive sulfene, which cannot be isolated but reacts further to give products, one of which may be the alkene that is the dimer of RCH. Reactions of sulfenes in situ are also common (e.g., see 16-62). 

Reaction of sulfonyl halides with tertiary amines and diazoalkanes... 

Closely related is the reaction of tertiary amines with sulfonyl halides that contain an a hydrogen. In this case the initial product is the highly reactive sulfene, which cannot be... 

HINSBERG REACTION. Reaction of primary and secondary amines with sulfonyl halides to give sulfanamides because the products front primary amines are soluble in alkali and those from secondary amines are not. and since tertiary amines do not react, this method is useful for the sepantlion and identification of amines. 

Amino-l,2,4-thiadiazoles (16) readily yield monoacylated derivatives of type (129) under the usual conditions whereas both monoacyl and diacyl derivatives (130 and 131, respectively) are easily obtained from the 3-amino isomers (65AHC(5)119, 70CB1805). In a similar manner the 3-amino-l,2,4 thiadiazoles produce mono- and di-sulfenamide derivatives when treated with sulfenyl halides. In general, the reactions of 3-amino- and 5-amino-1,2,4-thiadiazoles with sulfonyl halides under basic conditions produce only low yields of the desired derivatives. Sulfonamides of type (132) are best prepared by ring synthesis methods as illustrated in Scheme 55 (75LA1961). 

Several reactions describing epimerization in the sugar moiety of a nucleotide by way of an anhydroderivate have been discussed (see pp. 363 and 368). The introduction of sulfonyl groups into nucleotides has had limited application. Nucleotides react with sulfonyl halides to form mixed anhydrides... 

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