1,4-Dichalcogenins: Synthesis from Dichloroethenes and Elemental Chalcogens in a Hydrazine Hydrate–Potassium Hydroxide System

Nikonova, V. S.; Grabel’nykh, V. A.; Богданова, Ю. Н.; Sosnovskaya, Nina; Istomina, N. V.; Russavskaya, N. B.; Розенцвейг, И. Б.; Корчевин, Н. А.

doi:10.1134/s1070363221050091

Cited by 2 publications

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“…It should be emphasized that 2,3-dichloropropene, the key reagent in the synthesis of organochalcogen compounds by our methodology [ 30 , 31 , 32 , 33 , 34 , 35 , 36 ], is a large tonnage waste of organochlorine production, which requires utilization. Another technology-related feedstock is elemental sulfur.…”

Section: Introductionmentioning

confidence: 99%

“…Bis(chloropropenyl)sulfide 1 was obtained from 2,3-dichloropropene and elemental sulfur in the basic-reductive system hydrazine hydrate–KOH, which is successfully employed in the synthesis of organochalcogen compounds [ 34 , 35 , 36 ]. At the same time, the cyclization of compound 1 to thiophene derivatives effectively proceeded in acetonitrile [ 32 , 33 ].…”

Section: Introductionmentioning

confidence: 99%

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Heterocyclization of Bis(2-chloroprop-2-en-1-yl)sulfide in Hydrazine Hydrate–KOH: Synthesis of Thiophene and Pyrrole Derivatives

et al. 2022

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The article is devoted to heterocyclization of bis(2-chloroprop-2-en-1-yl)sulfide which proceeds in hydrazine hydrate–alkali medium and leads to formation of thiophene and pyrrole derivatives: previously described 4,5,9,10-tetrahydrocycloocta[1,2-c;5,8-c’]dithiophene, as well as unknown hydrazone of 5-methylidene-3-methyldihydrothiophen-2-one and 1-amino-2-(propynylsulfanylpropenylsulfanyl)-3,5-dimethylpyrrole. Tentative mechanisms for the formation of the heterocyclic products are discussed. Obtained hydrazone of 5-methylidene-3-methyldihydrothiophen-2-one was used for the synthesis of a range of azine derivatives and in oxidation process with SeO2. The found reactions open up expedient approaches to the formation of various hardly accessible thiophene and pyrrole compounds from 2,3-dichloropropene and elemental sulfur as starting reagents.

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