Reaction of selenium dibromide with divinyl sulfide

Russian Journal of General Chemistry -     

Reaction of anils with vinyl butyl sulfide

Summary In the presence of BF₃, vinyl butyl sulfide reacts with benzylideneaniline, benzylidene-o-toluidine, N-benzyl-ideneanthranilic acid, benzylidene-p-anisidine and benzylidene-p-phenetidine to yield quinoline derivatives.     

Reaction of vinyl sulfoxides with sodium sulfide and polysulfides

Sodium sulfide and polysulfides readily (50–55°C, 3 h, aqueous medium) react with alkyl vinyl sulfoxides to afford bis(alkylsulfinylethyl)sulfides and-polysulfides in up to 75% yield. Under comparable conditions the reaction of divinyl sulfoxide with sodium sulfide proceeds by the mechanism of addition-cyclization and results in 1,4-dithiane-1-oxide and 1,4-oxathiane-4-oxide. Microwave activation of the studied reactions allows to increase their rate and efficiency.     

Trifluoroacetylation of divinyl sulfide

Conclusions The electrophilic attack of trifluoroacetic anhydride on divinyl sulfide results in replacing the-olefinic proton of only one double bond to give vinyl (2-trifluoroacetylvinyl) sulfide.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2402–2403, October, 1981.     

Reaction of diphenylcarbenepentacarbonyltungsten with ethyl vinyl ether in non-polar solvents

The reaction of (CO)₅WC(C₆H₅)₂ with ethyl vinyl ether in benzene or pentane yields predominantly the two metathesis products 1,1-diphenyl-ethylene and 1-ethoxy-2,2-diphenylethylene along with some 1-ethoxy-2,2-diphenylcyclopropane.     

Conformational structure of divinyl sulfide

The potential of internal rotation about the bond for vinyl methyl sulfide is applied with some modifications to rotation about the analogous bonds in the divinyl sulfide molecule. The potential energy map of divinyl sulfide is discussed with regard to the excited torsional vibrational states. Three stable conformers with approximately identical energies were established. For a complete picture of the rotational isomerism it is also necessary to take account of the torsional vibrational stationary states with large amplitude.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1531–1535, July, 1991.     

The reaction of selenium dichloride with divinyl sulfide

A synthesis of novel selenium heterocycles based on the reaction of selenium dichloride with divinyl sulfide has been described. At −50 °C the reaction affords 2,6-dichloro-1,4-thiaselenane in quantitative yield. At room temperature the reaction gives 2,6-dichloro-1,4-thiaselenane and 5-chloro-2-chloromethyl-1,3-thiaselenolane. Upon standing in chloroform solution, 2,6-dichloro-1,4-thiaselenane undergoes spontaneous rearrangement to 5-chloro-2-chloromethyl-1,3-thiaselenolane. Under the action of pyridine, 2,6-dichloro-1,4-thiaselenane is converted to 2-chloromethyl-1,3-thiaselenole in 95% yield.     

Reaction of selenium dichloride with divinyl telluride

Russian Journal of Organic Chemistry -     

Reaction of thioxophosphorane sulfenyl bromides with ethyl vinyl ether: Mechanistic and synthetic aspects

The mechanistic and synthetic aspects of the addition reaction of thioxophosphorane sulfenyl bromide with ethyl vinyl ether were studied in detail by NMR techniques. It has been found that the regiospecific, primary product of the reaction, 1-bromo-1-ethoxy-2S(dialkoxythiophosphoryl)ethane I, is unstable and undergoes slow decomposition to give four compounds. The formation of thiophosphoryl derivatives, vinyl ethers II and III, aldehyde IV, and the symmetrical hemiacetal anhydride V, has been considered in terms of a carbocation intermediate. By choice of the appropriate reaction conditions, the aldehyde IV can be obtained in very high yield.     

Cycloaddition of primary phosphines to divinyl sulfide

Primary phosphines reacted with divinyl sulfide under radical initiation conditions (AIBN, 65–70°C, reactant molar ratio 1:1) according to the addition-cyclization pattern to give 4-substituted 1,4-thiaphosphinanes which underwent almost quantitative oxidation with oxygen or elemental sulfur, yielding the corresponding 4-substituted 1,4-thiaphosphinane oxides (sulfides). The reaction of 4-(2-phenylethyl)-1,4-thiaphosphinane with methyl iodide afforded 4-methyl-4-(2-phenylethyl)-1,4-thiaphosphinanium iodide with high chemoselectivity.