Quantum Chemical Study of Organic Reactions Mechanisms. XIII. The Reaction of Propargyl Chloride with Potassium 1,2-Ethandithiolate in the System Hydrazine Hydrate–KOH: Heterocyclization Paths

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Quantum chemical modeling of the mechanism of interaction of propargyl chloride with potassium 1,2-ethanedithiolate in the hydrazine hydrate–KOH system was carried out using the combined approach CCSD(T)/6-31+G*//B3LYP/6-311++G**. The elementary stages of the reaction and possible routes for the heterocyclization of the initial intermediates have been found. Under experimental conditions at a reaction temperature of 40-42°C, 6 hours, 2-methyl-5,6-dihydro-1,4-dithiine was obtained with a yield of 25% and 4,7-dithiadecadiine-2,8 with a yield of 24%. At a temperature of –10 ÷ –15°С, cyclic products are not formed.

Sobre autores

E. Chirkina

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences; Angarsky State Technical University, ul. Chaikovskogo

Autor responsável pela correspondência
Email: chirkina_ea@mail.ru
ORCID ID: 0000-0002-1733-0685
Rússia, Favorskogo, 1, Irkutsk, 664033; ul. Chaikovskogo, 60, Angarsk, 665835

V. Grabelnykh

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: chirkina_ea@mail.ru
ORCID ID: 0000-0003-1067-7755
ul. Favorskogo, 1, Irkutsk, 664033

N. Korchevin

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences; Angarsky State Technical University, ul. Chaikovskogo

Email: chirkina_ea@mail.ru
Scopus Author ID: 0000-0001-5729-9080
Favorskogo, 1, Irkutsk, 664033; ul. Chaikovskogo, 60, Angarsk, 665835

L. Krivdin

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences; Angarsky State Technical University, ul. Chaikovskogo

Email: chirkina_ea@mail.ru
ORCID ID: 0000-0003-2941-1084
Rússia, Favorskogo, 1, Irkutsk, 664033; ul. Chaikovskogo, 60, Angarsk, 665835

I. Rosenzweig

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: chirkina_ea@mail.ru
ORCID ID: 0000-0001-7817-7816
Rússia, , ul. Favorskogo, 1, Irkutsk, 664033

Bibliografia

  1. Chirkina E.A., Grabelnykh B.A., Korchevin H.A., Krivdin L.B., Ushakov I.A., Rozentsveig I.B. Structural Chemistry, 2023, 34, 2263–2272. doi: 10.1007/s11224-023-02199-9
  2. Levanova E.P., Grabelnykh V.A., Vahrina V.S., Albanov A.I., Klyba L.V., Russavskaya N.V., Korchevin N.A., Rozentsveig I.B. J. Sulfur Chem. 2014, 35, 179–187. doi: 10.1080/17415993.2013.849704
  3. Becke A.D. J. Chem. Phys. 1993, 98, 5648-5652. doi: 10.1063/1.464913
  4. Lee C., Yang W., Parr R.G. Phys. Rev. B 1988, 37, 785-789. doi: 10.1103/PhysRevB.37.785
  5. Леванова Е.П., Никонова В.С., Грабельных В.А., Руссавская Н.В., Албанов А.И., Розенцвейг И.Б., Корчевин Н.А. ЖОрХ. 2016, 52, 540–541. [Levanova E.P., Nikonova V.S., Grabelnykh V.A., Russavskaya N.V., Albanov A.I., Rozentsveig I.B., Korchevin N.A. Russ. J. Org. Chem. 2016, 52, 615–623. doi: 10.1134/S1070428016050018
  6. Gaussian 09, Revision C.01, Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Mennucci B., Petersson G.A., Nakatsuji H., Caricato M., Li X., Hratchian H.P., Izmaylov A.F., Bloino J., Zheng G., Sonnenberg J.L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A., Peralta J.E., Ogliaro F., Bearpark M., Heyd J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Rega N., Millam J.M., Klene M., Knox J.E., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Martin R.L., Morokuma K., Zakrzewski V.G., Voth G. A., Salvador P., Dannenberg J.J., Dapprich S., Daniels A.D., Farkas Ö., Foresman J.B., Ortiz J.V., Cioslowski J., and Fox D.J., Gaussian, Inc., Wallingford CT, 2009.
  7. Хусайнов З.К., Ойматова Х.Х., Сафаров М.М., Тургунбоев М.Т. Вестник Таджикского нац. универ. Сер. естеств. наук. 2019, 2, 196–203.
  8. Современные методы органического синтеза. Ред. Т.В. Мандельштам, Б.В. Иоффе, Ю.П. Арцыбашева. Ленинград, 1980.
  9. Berne B.J., Tuckerman M., Martyna G. J. Chem. Phys. 1991, 94, 6811. doi: 10.1063/1.460259
  10. González C., Schlegel H.B. J. Phys. Chem. 1990, 94, 5523–5527. doi: 10.1021/j100377a021
  11. González C., Schlegel H.B. J. Chem. Phys. 1991, 95, 5853. doi: 10.1063/1.461606

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