Synthesis of cyclic sulfides

A general scheme is proposed for the synthesis of 4-alkylthiacyclohexanes by reaction of 1-alken-3-ylmagnesium halides with ethylene episulfide and subsequent cyclization of the resulting 3-alkylpent-4-ene-1-thiols under the in-fluence of UV irradiation. 4-Amyl- and 4-octylthiacyclohexanes, together with 2-methyl-3-octylthiacyclopentane, were obtained, respectively, from 1-octen-3-ylmagnesium bromide, 1-undecen-3-ylmagnesium chloride, and ethylene episulfide.See [1] for communication. VII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1622–1624, December, 1977.     

Synthesis of cyclic sulfides

3-Phenylthiacyclohexane and 2-methyl-4-phenylthiacyclopentane were synthesized by reaction of styrene episulfide with allylmagnesium bromide and subsequent photochemical cyclization of the resulting 2-phenyl-4-pentene-1-thiol.     

Synthesis of cyclic sulfides

A new method for the synthesis of bicyclic sulfides consisting of the reaction of cycloolefin sulfides with vinylmagnesium or allylmagnesium bromides and the subsequent intramolecular cyclization of the resulting unsaturated mercaptans has been proposed. By using this method, from cyclohexene sulfide we have synthesized 1-thiadecalin and 2-methyl-1-thiahydrindan; and complexes of these substances with mercuric chloride, and their methiodides and sulfones have been obtained.The results of this work were reported in part at the XI-th Scientific Meeting on the Chemistry of Organosulfur Compounds of Petroleum and Petroleum Products (Ufa, 1968).     

Synthesis of cyclic sulfides

2,8-Dimethyl-1-thiahydrindan and 9-methyl-1-thiadecalin, respectively, were obtained by the reaction of 1-methyl-1-cyclohexene episulfide with allylmagnesium bromide and subsequent intramolecular cyclization of the resulting 1-methyl-2-allylcyclohexane-1-thiol by the action of sulfuric acid or UV irradiation. The cyclization proceeds stereospecifically.See [1] for communication V.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1186–1188, September, 1972.     

Synthesis of cyclic sulfides

Two isomers of 2,3-dimethyl-1-thiahydrindane and two isomers of 4-methyl-1-thiadecali were obtained by the reaction of cyclohexene episulfide with crotylmagnesium bromide and subsequent cyclization of the resulting 2-(-methyl--propenyl)-1-cyclohexanethiol by the action of 75% sulfuric acid and UV irradiation.See [3] for communication IV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 622–625, May, 1972.     

Synthesis of cyclic sulfides

2-Methyl-, 2,5-dimethyl-, 2-n-butyl-5-methylthiacyclopentanes, thiacyclohexane, and 2-methyl- and 2-n-butylthiacyclohexanes were obtained by the reaction of ethylene, propene, and 1-hexane episulfides with allylmagneisum bromide with subsequent cyclization of the alkenethiols thus formed.See [2] for Communication II.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1614–1616, December, 1970.     

Polymerization of cyclic sulfides

The ring-opening polymerizations of cyclic sulfides containing three-, four-, and fivemembered rings were studied. In conjunction with these polymerizations, the relative basicities of the cyclic sulfides employed were also investigated. Polymerizations were effected by the use of phosphorus pentafluoride, boron trifluoride ethyl ether, triethylaluminum, and trimethyloxonium tetrafluoroborate. The resulting polymers were oxidized to the sulfones and differential thermal analyses were obtained on the sulfide polymers as well as the sulfone analogs.     

Synthesis of heterocyclic sulfides

2-Allylcyclopentane-1-thiol is cyclized by treatment with 75% sulfuric acid and with UV light to 2-methyl-1-thiabicyclo[3, 3, 0]octane and 1-thiabicyclo[4, 3, 0]nonane, respectively. The cyclization is stereospecific.For Part I, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1185–1187, September, 1970.     

Reactivity of cyclic sulfides in reactions with quinones

Sulfonium salts are obtained by the reaction of cyclic sulfides with 1,4-benzoquinone and 5,8-quinolinedione in an acidic medium. It is shown by the method of concurrent reactions that the introduction of alkyl substituents into molecules of thiacyclopentane and thiacyclohexane decreases the reactivity of the sulfides. Quinolinedione is less reactive towards sulfides than is benzoquinone.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 891–894, July, 1986.     

Synthesis of monosubstituted divinyl sulfides

Conclusions Sodium ethenethiolate obtained from readily available divinyl sulfide reacts with allyl chloride and phenylacetylene to form vinyl 1-propenyl sulfide and vinyl styryl sulfide.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 699–701, March, 1986.     

Synthesis ofα-polynitroalkyl sulfides

Conclusions The reaction of the salts of polynitroalkanes with sulfenyl chlorides proceeds by the C-sulfenylation scheme, with the formation of the corresponding-polynitroalkyl sulfides.     

Dipole moments and UV spectra of some two-ring cyclic sulfides

The dipole moments and UV spectra of 17 compounds of the 5,6-tetramethylene- and 5,6-trimethylenethiapyran series and their saturated analogs were measured. The dipole moments of the investigated compounds range from 1.2 to 2.0 D. The effect of the size of the saturated side ring and the position of the unsaturated bonds in the sulfur-containing heteroring on the dipole moments is demonstrated. The UV spectra of the compounds with, respectively, five- and six-membered saturated side rings are virtually identical. The position of the bands is determined primarily by the structure of the heteroring.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 744–747, June, 1978.