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Kovregin, A. N.; Sizov, A. Yu.; Ermolov, A. F.

doi:10.1023/a:1019669820268

Cited by 6 publications

(11 citation statements)

References 2 publications

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“…25 2-Cyano-1,3,3,3-tetrafluoropropenesulfenyl chloride synthesised in this reaction is a labile compound; on heating, it undergoes intramolecular cyclisation involving the nitrile group to give isothiazole. 77 A similar intramolecular cyclisation of the intermediate sulfenyl chloride involving the nitrile group is observed in the chlorolysis of tert-butyl (2-cyano-1,2-difluorovinyl) sulfide. 77 Simultaneously, the double bond is chlorinated.…”

Section: Chemical Propertiesmentioning

confidence: 70%

“…77 A similar intramolecular cyclisation of the intermediate sulfenyl chloride involving the nitrile group is observed in the chlorolysis of tert-butyl (2-cyano-1,2-difluorovinyl) sulfide. 77 Simultaneously, the double bond is chlorinated.…”

Section: Chemical Propertiesmentioning

confidence: 70%

“…The reaction can be followed by monitoring the evolution of hydrogen chloride. 59 When bases, for example, triethylamine, are added as HCl acceptors, resinification of the reaction mixture takes place.…”

Section: A Ab B-elimination In Fluorine-containing Sulfidesmentioning

confidence: 99%

“…18 In the case where the sulfur atom carries a good leaving group, for example, a benzyl group, chlorolysis proceeds further to give sulfenyl chlorides. 18,77 Bromination of 2,2-difluoro-1,1-diphenylthioethylene in methanol is accompanied by conjugate electrophilic addition, as indicated by the formation of methyl bromodifluoroacetate after hydrolysis of the intermediate compound formed. 109 Some perfluoroalkenyl and perfluorocycloalkenyl benzyl sulfides having an electron-deficient multiple bond undergo chlorolysis at the S7Bn bond with retention of the vinyl fragment.…”

Section: Chemical Propertiesmentioning

confidence: 99%

“…109 Some perfluoroalkenyl and perfluorocycloalkenyl benzyl sulfides having an electron-deficient multiple bond undergo chlorolysis at the S7Bn bond with retention of the vinyl fragment. 3 A number of b-functionally substituted polyfluoroalkenesulfenyl chlorides have been prepared by chlorolysis of tert-butyl sulfides by chlorine 77 or sulfuryl chloride. 25 2-Cyano-1,3,3,3-tetrafluoropropenesulfenyl chloride synthesised in this reaction is a labile compound; on heating, it undergoes intramolecular cyclisation involving the nitrile group to give isothiazole.…”

Section: Chemical Propertiesmentioning

confidence: 99%

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Fluorine-containing alkyl(aryl) vinyl sulfides

Sizov¹,

Kovregin²,

Ermolov³

2003

Russ. Chem. Rev.

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Approaches to the synthesis of fluorine-containing Approaches to the synthesis of fluorine-containing alkyl(aryl) vinyl sulfides, their reactions with electrophilic and alkyl(aryl) vinyl sulfides, their reactions with electrophilic and nucleophilic reagents and the behaviour in cycloaddition and nucleophilic reagents and the behaviour in cycloaddition and oxidation reactions are considered systematically. The bibliogra-oxidation reactions are considered systematically. The bibliography includes 136 references phy includes 136 references. .

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Section: Chemical Propertiesmentioning

confidence: 70%

Section: Chemical Propertiesmentioning

confidence: 70%

Section: A Ab B-elimination In Fluorine-containing Sulfidesmentioning

confidence: 99%

Section: Chemical Propertiesmentioning

confidence: 99%

Section: Chemical Propertiesmentioning

confidence: 99%

See 3 more Smart Citations

Fluorine-containing alkyl(aryl) vinyl sulfides

Sizov¹,

Kovregin²,

Ermolov³

2003

Russ. Chem. Rev.

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Reactions of α‐Fluorine‐Containing β‐Functionalized Vinyl Sulfides with N‐Nucleophiles.

Kovregin¹,

Sizov²,

Ermolov³

2002

ChemInform

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mercaptans, thioethersmercaptans, thioethers (acyclic compounds) P 0430 -094Reactions of α-Fluorine-Containing β-Functionalized Vinyl Sulfides with N-Nucleophiles.-The reaction of vinyl sulfides (I) with primary or secondary amines proceeds with fluorine substitution to afford α-aminovinyl sulfides in good yields. These can undergo thermal cyclization to quinolinones under incorporation of the ester group. Incorporation of the trifluoromethyl group into cyclization of β-cyano-β-trifluoromethylvinyl sulfides [e.g. (IIIb)] affords 4-fluoroquinolines, which are not stable and hydrolyze to quinolinones. The reactions with arylhydrazines (V), (VII) and amidines (IX) directly proceed with cyclization at the functional group. -(KOVREGIN, A. N.; SIZOV, A. YU.; ERMOLOV, A. F.; Russ.

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