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Chemistry of Heterocyclic Compounds | 1996

Oxidation reactions of 4H-chalcogenopyrans

B. I. Drevko; M. I. Smushkin; V. G. Kharchenko

We have studied the oxidation of 4H-chalcogenopyrans and chalcogenopyrylium salts by lead tetraacetate. We have established that the major reaction products on oxidation of 2,6-diphenyl-4H-thiopyran and selenopyran are 2,6-diphenyl-4H-thio(seleno)pyran-4-ones, while 2-benzoyl-5-phenyl(seleno)thiophenes are formed as impurities. The major product on oxidation of 2,6-diphenyl-4H-pyran is 2-benzoyl-5-phenylfuran. We have shown that 2,4,6-triphenyl-4H-pyran does not undergo oxidation by hydrogen peroxide in neutral medium, in contrast to its S and Se analogs. This supports the hypothesis that the heteroatom participates in the oxidation process.


Chemistry of Heterocyclic Compounds | 1999

Photochemical oxidation of 4h-seleno(thio)pyrans

B. I. Drevko; L. A. Fomenko; M. A. Suchkov; V. G. Kharchenko

Oxidation of solutions of 4H-thiopyrans and 4H-selenopyrans to the corresponding heteroaromatic cation bromide occurs on irradiation with ultraviolet light in the presence of CBr4. Reaction takes place by a free radical chain mechanism. The presence of CHBr3 and C2Br6 in the reaction mixture was detected chromatographically.


Chemistry of Heterocyclic Compounds | 1999

New method for synthesis of 2,5-disubstituted thiophenes

T. I. Gubina; B. I. Drevko; L. N. Fedina; S. M. Rogacheva; V. G. Kharchenko

The use of hydrogen sulfide at the moment of formation is proposed for the recyclization of furans into thiophenes in acidic media. The advantages of this method are shown.


Chemistry of Heterocyclic Compounds | 1995

STUDY OF OXIDATION REACTIONS OF 4H-SELENOPYRANS

B. I. Drevko; M. I. Smushkin; L. A. Fomenko; V. G. Kharchenko

The oxidation of 4H-4R-2,6-diphenylselenopyrans was studied. This reaction was found to depend on the presence of substituents at C(4) of the heterocycle and the reaction conditions.


Chemistry of Heterocyclic Compounds | 1989

Oxidation of 2,4,6-triaryl-4H-thio(seleno)pyrans with selenium dioxide

B. I. Drevko; L. A. Fomenko; V. G. Kharchenko

The oxidation of 2,4,6-triaryl4-H-thio(seleno)pyrans with selenium oxide in pyridine was studied. It is shown that the corresponding 2,4-diaryl-5-aroyl-thiophenes and -selenophenes are formed as a result of the oxidation.


Chemistry of Heterocyclic Compounds | 1984

Reactions of 1,5-diketones with hydrogen selenide in the presence of trifluoroacetic acid

V. G. Kharchenko; B. I. Drevko

Two competing pathways were found in the transformations of 1,5-diketones and the 4H-selenopyrans formed from these diketones upon reaction with CF3CO2H in the presence of hydrogen selenide entailing disproportionation and the electrophilic addition of hydrogen selenide.


Chemistry of Heterocyclic Compounds | 1994

Synthesis of 5,6-polymethyleneselenopyryllium salts

B. I. Drevko; L. A. Fomenko; M. I. Smushkin; O. I. Zhukov; E. V. Drevko; V. G. Kharchenko


Chemistry of Heterocyclic Compounds | 1998

Recyclization of 4H-pyrans to 4H-selenopyrans

B. I. Drevko; M. A. Suchkov; V. G. Kharchenko


Chemistry of Heterocyclic Compounds | 1991

Oxidation of 4-H-selenopyrans

S. N. Petrakov; B. I. Drevko; L. A. Fomenko; V. G. Kharchenko


Chemistry of Heterocyclic Compounds | 1984

Transformations of 2,4,6-triaryl-2,6-di(hydroseleno)-1-selenocyclohexanes on their reaction with acids

V. G. Kharchenko; B. I. Drevko

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L. A. Fomenko

Saratov State University

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M. I. Smushkin

Saratov State University

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M. A. Suchkov

Saratov State University

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I. V. Antipova

Saratov State University

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L. N. Fedina

Saratov State University

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S. N. Petrakov

Saratov State University

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T. I. Gubina

Saratov State University

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