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

doi:10.1023/a:1013098921520

Cited by 3 publications

(4 citation statements)

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“…NEt 3 represent a convenient method for the synthesis of b-functionally substituted vinyl sulfides and ketene dithioacetals. 44 Undoubtedly, the first step of this reaction involves dehydrofluorination of the CH-acid to give fluoroalkene, which is attacked in situ by the anion generated upon the action of BF 3 . NEt 3 on the thiol.…”

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

confidence: 99%

“…In particular, bifunctional thiols such as ethane-1,2-dithiol and mercaptoethanol are converted into cyclic thioacetals 13 in high yields. 44 A method for the synthesis of vinyl sulfides by the reaction of perfluoropropylene with thiols in the presence of a solution of potassium carbonate in aqueous acetone has been patented. 45 When fluoroalkenes are made to react with sodium or lithium thiolates, fluorinated vinyl sulfides mixed with the addition products are formed.…”

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

confidence: 99%

“…The reaction is accompanied by intramolecular dehydrofluorination and cyclisation giving rise to substituted N-aryl-2-(1-methoxycarbonyltrifluoroethylidene)-2,3dihydrothiazoles. 76 The reactions of chlorofluoromethanesulfenyl chlorides with triethylamine furnish vinyl sulfides 35. This can be a result of electrophilic replacement of hydrogen in enamine 36.…”

Section: Fluorine-containing Alkyl(aryl) Vinyl Sulfidesmentioning

confidence: 99%

“…A similar reaction is also typical of o-sulfenylated phenols. 75 When reacting with potassium hydroxide, ethyl 2-(1-trifluoromethylvinylthio)acetoacetates 74a,b are deacetylated to give the corresponding acids. 21 The vinylthio group does not participate in the reaction.…”

Section: -Mec6h4so3hmentioning

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: A Ab B-elimination In Fluorine-containing Sulfidesmentioning

confidence: 99%

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

confidence: 99%

Section: Fluorine-containing Alkyl(aryl) Vinyl Sulfidesmentioning

confidence: 99%

Section: -Mec6h4so3hmentioning

confidence: 99%

See 2 more Smart Citations

Fluorine-containing alkyl(aryl) vinyl sulfides

Sizov¹,

Kovregin²,

Ermolov³

2003

Russ. Chem. Rev.

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ChemInform Abstract: Reactions of 1,3,3,3‐Tetrafluoro‐2‐methoxycarbonylpropenesulfenyl Chloride with Enamines.

Kovregin¹,

Sizov²,

Ermolov³

2002

ChemInform

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2002sulfuration, sulfonation, S-alkylation sulfuration, sulfonation, S-alkylation O 0245 -049Reactions of 1,3,3,3-Tetrafluoro-2-methoxycarbonylpropenesulfenyl Chloride with Enamines.-Reactions of the title sulfenyl chloride (I) with enamines derived from β-oxo acids affords sulfenylation products [cf. (III)]. Unlike enamines with a free amino group, reactions of N-aryl-substituted enamines (V) are accompanied by cyclization to furnish thiazole derivatives (VI). -(KOVREGIN, A. N.; SIZOV, A. YU.; ERMOLOV, A. F.; Russ.

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Increasing Scope of Clickable Fluorophores: Electrophilic Substitution of Ylidenemalononitriles

et al. 2020

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Recently, we demonstrated that ylidenemalononitriles (YMs) react with amines to form cyclic amidines and that the starting linear YMs are nonemissive in solution and the cyclic amidines are fluorescent. These turn-on systems were of interest to us because of their potential as biosensors and synthons for accessing functionalized pyridines. While our original method was promising, several limitations persisted, including access to more functionalized and polar-solvent-soluble structures as well as increased control over the rate of cyclization. Herein, we report a new approach that allows the electrophilic substitution of YMs. These substituted YMs exhibit faster turn-on rates, color tunability, access to polar-solvent-soluble species, and increased control over cyclization rate. This allowed us to significantly expand the fluorophore's chemical space.

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Untitled

Cited by 3 publications

References 0 publications

Fluorine-containing alkyl(aryl) vinyl sulfides

Fluorine-containing alkyl(aryl) vinyl sulfides

ChemInform Abstract: Reactions of 1,3,3,3‐Tetrafluoro‐2‐methoxycarbonylpropenesulfenyl Chloride with Enamines.

Increasing Scope of Clickable Fluorophores: Electrophilic Substitution of Ylidenemalononitriles

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