ISSN:
1573-9171
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Conclusions 1. Sulfonium dinitroylides $$R_2 \mathop S\limits^ + - C(NO_2 )_2^ - $$ are cleaved at the $$S - C_{NO_2 } $$ bond by electrophiles such as halogens (chlorine, bromine, bromine chloride), sulfuryl chloride, hydrogen halides (chloride and bromide), giving the corresponding di- or monohalodinitromethanes. 2. Phenylsulfenyl chloride reacts with $$(CH_3 )_2 \mathop S\limits^ + - C(NO_2 )_2^ - $$ , forming dinitrobis(phenylthio)methane and dtnitrophenylthiomethane. 3. Compounds containing a positive halogen (N-haloamides, N-chloroalkylnitramines, BrONO2, SO2FCl, CH3CO2C1) react with $$(CH_3 )_2 \mathop S\limits^ + - C(NO_2 )_2^ - $$ to give the corresponding dihalodinitromethanes. 4. Electrophiles (chlorine, bromine, phenylsulfenyl chloride) are capable of cleaving the $$S - C_{NO_2 } $$ bond of dinitromethylsulfonium salts, forming the corresponding monosubstituted dinitromethane, ClCH(NO2)2, BrCH(NO2)2, and PhSCH(NO2)2. On the basis of our results we propose a scheme for the reaction of $$(CH_3 )_2 \mathop S\limits^ + - C(NO_2 )_2^ - $$ with phenylsulfenyl chloride and compounds containing a positive halogen.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00921507
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