Cycloaddition of Thiourea to Tri(1-propenyl)amine

Russian Journal of General Chemistry -     

Reactions of triads Se8KOHDMSO,Se8KOHDMSO,TeKOHHMPA with acetylenes

A new general approach to anionic transformations of acetylenes using superbasic media has been developed. It allows series of new reactions which are not undergone by acetylene under conventional conditions. The triads Se₈KOHdimethylsulfoxide (DMSO), Se₈KOHDMSO, TeKOH-hexamethyl-phosphorictriamide (HMPA) are proposed as new effective reagents for the preparation of unsaturated compounds of sulfur, selenium and tellerium. A series of reactions of acetylene with sulfur, selenium and tellerium proceeding in DMSO or HMPA in the presence of alkali and water at 80–120° leading to divinyl sulfide, divinyl selenide and divinyl teluride in 25–80% yields have been found. Thiophen, di-1-(1,3-butadienyl) sulfide, 1-vinyl-2-thiabicyclo[3.2.0]hept-3-ene, and dihydrothiophen have been obtained by the reaction of vinylacetate with sulfur. The reaction of vinylacetylene with selenium affords selenophen, di-1-(1,3-butadienyl) selenide, 1-vinyl-2-selenabicyclo[3.2.0]hept-3-ene, methyl (1-(1,3-butadienyl) sulfide, and methylthiomethyl 1-(1,4-butadienyl) selenide, vinyl 1-(1,3-butadienyl) sulfide, and methylthiomethyl 1-(1,3-butadienyl) selenide (the latter two with DMSO participation). The reaction of vinylacetate with tellerium gives mainly di-1-(1,3-butadienyl) telluride. A series of reactions between DMSO and selenium leading to dimethyl sulfide, dimethyl sulfoselenide, and methylthiomethyl selenide have been observed.     

Selective synthesis of di(propen-1-yl)sulfone and di(propen-1-yl)sulfoxide

Convenient selective methods of synthesis of the title compounds, based on oxidation of di(propen-1-yl)sulfide with 30% H₂O₂, have been developed.Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 664033 Irkutsk. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 3, pp. 675–679, March, 1992.     

A simple synthesis of 2-methyl-1,4-dithiacycloheptane from diallyl sulfide and hydrogen sulfide

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, PP. 2669–2670, November, 1990.     

Regioselectivity in the addition of alkanethiols to vinylacetylene in superbasic media of alkali-metal hydroxides in dimethyl sulfoxide

Conclusions The reaction of vinylacetylene with alkanethiols is largely directed toward the formation of alkyl 1,3-butadien-l-yl sulfide with increasing basicity of the system consisting of an alkali-metal hydroxide and DMSO. A reduction in the basicity facilitates the formation of alkyl 2,3-butadien-l-yl sulfide.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2800–2803, December, 1985.     

Bound States in the Continuum in Magnetophotonic Metasurfaces

JETP Letters - We analyze the enhancement mechanisms of magneto-optical effects in all-dielectric metasurfaces caused by the bound state in the continuum resonance. In a structure under study, a...     

Formation of diallyl disulfide from diallyl sulfide in the H2S-DMSO system

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1708–1709, July, 1991.     

Reactions of Tri(1-propenyl)amine with Elemental Sulfur

The reaction of tri(1-propenyl)amine with elemental sulfur in bipolar aprotic solvent (DMF'DMSO) at 50°C within 1.5 h furnished 5-methyl-2-ethylthiazole in 62% yield. 2H'5H-5-methyl-2-ethyl-thiazole, 2-hydroxy-5-methylbenzaldehyde were found among the side products. The formation paths of thecompounds obtained are suggested.     

Behavior of Allylamines in the System KOH-DMSO

Isomerization of triallylamine in the system KOH-DMSO at 90-100°C leads to formation of tris-(1-propenyl)amine in quantitative yield. Under similar conditions, diallyl(ethyl)amine is converted into ethyl-bis(1-propenyl)amine, 1-ethyl-3-methylcyclohexane. Diallylamine in KOH-DMSO gives rise to a complexmixture of products consisting of bis(1-propenyl)amine, methylbis(1-propenyl)amine, 1-ethyl-3-methylcyclo-hexane, and 2-ethyl-3,5-dimethylpiperidine. Ways of formation of these products are discussed.