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Nitroylides 2. Reaction of sulfonium dinitroylides with electrophiles Full article

Journal Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science
ISSN: 2376-8444 , E-ISSN: 0568-5230
Output data Year: 1977, Volume: 26, Number: 1, Pages: 120-125 Pages count : 6 DOI: 10.1007/bf00921507
Authors Shevelev S.A. 1 , Semenov V.V. 1 , Fainzil'berg A.A. 1
Affiliations
1 N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

Abstract: 1. Sulfonium dinitroylides are cleaved at the 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 , forming dinitrobis(phenylthio)methane and dtnitrophenylthiomethane. 3. Compounds containing a positive halogen (N-haloamides, N-chloroalkylnitramines, BrONO2, SO2FCl, CH3CO2C1) react with to give the corresponding dihalodinitromethanes. 4. Electrophiles (chlorine, bromine, phenylsulfenyl chloride) are capable of cleaving the 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 with phenylsulfenyl chloride and compounds containing a positive halogen.
Cite: Shevelev S.A. , Semenov V.V. , Fainzil'berg A.A.
Nitroylides 2. Reaction of sulfonium dinitroylides with electrophiles
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1977. Т.26. №1. С.120-125. DOI: 10.1007/bf00921507 OpenAlex
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OpenAlex: W2328722392
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