Defluorination And Other Transformations of Perfluorinated Tetralin, Alkyltetralins and 4-Methyl-1,2-Dihydronaphthalene with Zinc in DMF. Synthesis of Perfluorinated 1-Ethyl- and 1-Methylnaphthalenes

V. R. Sinyakov; Синяков Владимир Рейнович; T. V. Mezhenkova; Меженкова Татьяна Владимировна; V. M. Karpov; Карпов Виктор Михайлович; Ya. V. Zonov; Зонов Ярослав Викторович

doi:10.31857/S0514749224080017

Defluorination And Other Transformations of Perfluorinated Tetralin, Alkyltetralins and 4-Methyl-1,2-Dihydronaphthalene with Zinc in DMF. Synthesis of Perfluorinated 1-Ethyl- and 1-Methylnaphthalenes

Autores: Sinyakov V.R.¹, Mezhenkova T.V.¹, Karpov V.M.¹, Zonov Y.V.¹
Afiliações:
1. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
Edição: Volume 60, Nº 8 (2024)
Páginas: 5-14
Seção: Articles
URL: https://freezetech.ru/0514-7492/article/view/676670
DOI: https://doi.org/10.31857/S0514749224080017
EDN: https://elibrary.ru/RBGJLW
ID: 676670

Citar

Texto integral

Acesso aberto
Acesso é fechado

Acesso está concedido
Acesso é fechado

Somente assinantes

Resumo

The interaction of perfluorotetralin with zinc in DMF followed by the treatment with water gave 1,1,2,2,3,3,4,4,5,6,8-undecafluorotetralin, perfluoro-2,2'-binaphthyl and octafluoronaphthalene. 1,2,3,4,6,7-Hexafluoro-5-(perfluoroethyl)naphthalene and perfluorinated 1-ethyl- and 1-vinylnaphthalenes were obtained from perfluoro-1-ethyltetralin by a similar reaction. Perfluoro-6-methyltetralin under similar conditions formed 1,2,4,5,6,8-hexafluoro-3-(trifluoromethyl)naphthalene and perfluoro-2-methylnaphthalene. The reaction of perfluoro-4-methyl-1,2-dihydronaphthalene with zinc in DMF resulted in the formation of perfluoro-1-methylnaphthalene. When perfluoro-1-ethyltetraline reacted with bromine-activated zinc in DMF, a mixture containing (perfluoro-4-ethylnaphthalene-1-yl)zinc bromide was formed, which was converted into 1,2,3,4,6,7-hexafluoro-5-(perfluoroethyl)naphthalene and perfluoro-4,4'-diethyl-1,1'-binaphthyl under the action of water and CuCl₂, respectively.

Palavras-chave

perfluorinated methyltetralin, ethyltetralin, naphthalene, methylnaphthalene, ethylnaphthalene, zinc, dimethylformamide

Texto integral

Bibliografia

Якобсон Г.Г., Штейнгарц В.Д., Ворожцов-мл. Н.Н. ЖВХО 1964, 9, 702–704. [Yakobson G.G., Shteingarts V.D., Vorozhtsov Jr. N.N. C.A. 1965, 62, 9078b].
Zakharova O.A., Goryunov L.I., Troshkova N.M., Ovchinnikova L.P., Shteingarts V.D., Nevinsky G.A. Eur. J. Med. Chem. 2010, 45, 270–274. doi: 10.1016/j.ejmech.2009.10.006
Zakharova O.A., Ovchinnikova L.P., Goryunov L.I., Troshkova N.M., Shteingarts V.D., Nevinsky G.A. Eur. J. Med. Chem. 2010, 45, 2321–2326. doi: 10.1016/j.ejmech.2010.02.009
Zakharova O.A., Ovchinnikova L.P., Goryunov L.I., Troshkova N.M., Shteingarts V.D., Nevinsky G.A. Bioorg. Med. Chem. 2011, 19, 256–260. doi: 10.1016/j.bmc.2010.11.027
Goryunov L.I., Zhivetyeva S.I., Nevinsky G.A., Shteingarts V.D. ARKIVOC. 2011, 8, 185–191. doi: 10.3998/ark.5550190.0012.814
Zakharova O.A., Ovchinnikova L.P., Zhivetyeva S.I., Goryunov L.I., Shteingarts V.D., Tretyakov E.V., Nevinsky G.A. Adv. Res. 2016, 6, 1–12. doi: 10.9734/AIR/2016/24265
Zhivetyeva S.I., Zakharova O.D., Ovchinnikova L.P., Baev D.S., Bagryanskaya I.Yu., Shteingarts V.D., Tolstikova T.G., Nevinsky G.A., Tretyakov E.V. J. Fluor. Chem. 192, 2016, 68–77. doi: 10.1016/j.jfluchem.2016.10.014
Zhivetyevaa S.I., Tretyakov E.V., Bagryanskaya I.Yu. J. Fluor. Chem. 2018, 206, 19–28. doi: 10.1016/j.jfluchem.2017.11.010
Leroux F., Jeschke P., Schlosser M. Chem. Rev. 2005, 105, 827–856. doi: 10.1021/cr040075b
Purser S., Moore P.R., Swallow S., Gouverneur V. Chem. Soc. Rev. 2008, 37, 320–330. doi: 10.1039/b610213c
Zhou Y., Wang J., Gu Z., Wang S., Zhu W., Aceña J.L., Soloshonok V.A., Izawa K., Liu H. Chem. Rev. 2016, 116, 422–518. doi: 10.1021/acs.chemrev.5b00392
Meanwell N.A. J. Med. Chem. 2018, 61, 5822–5880. doi: 10.1021/acs.jmedchem.7b01788
Wua J., Zhangc H., Ding X., Tan X., Shen H.C., Chen J., He W., Deng H., Song L., Cao W.
J. Fluor. Chem. 2019, 220, 54–60. doi: 10.1016/j.jfluchem.2019.02.002
Abula A., Z. Xu Z., Zhu Z., Peng C., Chen Z., Zhu W., Aisa H.A. J. Chem. Inf. Model. 2020, 60, 6242–6250. doi: 10.1021/acs.jcim.0c00898
Pozdnyakovich Yu.V., Shteingarts V.D. J. Fluor. Chem. 1974, 4, 283–296. doi: 10.1016/S0022-1139(00)80865-9
Pozdnyakovich Yu.V., Shteingarts V.D. J. Fluor. Chem. 1974, 4, 297–316. doi: 10.1016/S0022-1139(00)80866-0
Fadeev D.S., Chuikov I.P., Mamatyuk V.I. J. Fluor. Chem. 2016, 182, 53–60. doi: 10.1016/j.jfluchem.2015.12.003
Gething B., Patrick C.R., Smith B.J.K., Tatlow J.C. J. Chem. Soc. 1962, 190–193. doi: 10.1039/JR9620000190
Weigert F.J. J. Fluor. Chem. 1993, 61, 1–9. doi: 10.1016/S0022-1139(00)80410-8
Малышева В.В., Платонов В.Е., Якобсон Г.Г. Изв. АН. Сер. хим. 1974, 1669 [Malysheva V.V., Platonov V.E., Yakobson G.G. Bull. Acad. Sci. USSR. Div. Chem. Sci. 1974, 23, 1598].
Платонов В.Е., Малышева В.В., Якобсон Г.Г. Изв. СО АН СССР. Сер. хим. н. 1977, 2, 133 [Platonov V.E., Malysheva V.V., Yakobson G.G. Izv. Sib. Otd. Akad. Nauk SSSR. Ser. Khim. Nauk, C. A. 1977, 87, 134761d].
Синяков В.Р., Меженкова Т.В, Карпов В.М., Зонов Я.В. ЖОрХ. 2017, 53, 1786–1791. [Sinyakov V.R., Mezhenkova T.V., Karpov V.M., Zonov Ya.V. Russ. J. Org. Chem. 2017, 52, 1822–1827]. doi: 10.1134/S1070428017120065
Виноградов А.С., Краснов В.И., Платонов В.Е. ЖОрХ. 2008, 44, 101–107. [Vinogradov A.S., Krasnov V.I., Platonov V.E. Russ. J. Org. Chem. 2008, 44, 95–102]. doi: 10.1134/S1070428008010119
Hu C.M., Long F., Xu Z.Q. J. Fluor. Chem. 1990, 48, 29–35. doi: 10.1016/S0022-1139(00)82599-3
Krasnov V.I., Platonov V.E., Beregovaya I.V., Shchegoleva L.N. Tetrahedron. 1997, 53, 1797–1812. PII: SOO40-4020(96)01090-3
Виноградов А.С., Платонов В.Е. ЖОрХ. 2015, 51, 1419–1425. [Vinogradov A.S., Platonov Russ. J. Org. Chem. 2015, 51, 1388–1394]. doi: 10.1134/S107042801510005X
Miller A.O., Krasnov V.I., Peters D., Platonov V.E., Miethchen R. Tetrahedron Lett. 2000, 41, 3817–3819. doi: 10.1016/S0040-4039(00)00527-X
Фурин Г.Г., Малюта Н.Г., Платонов В.Е., Якобсон Г.Г. ЖОрХ. 1974, 10, 830–838.
Бардин В.В., Позднякович Ю.В., Штейнгарц В.Д. А.с. 491605 (1974). СССР. Б.И. 1975, № 42.
Karpov V.M., Mezhenkova T.V., Platonov V.E., Yakobson G.G. J. Fluor. Chem. 1985, 28, 121–127. doi: 10.1016/S0022-1139(00)85198-2
Zonov Y.V., Karpov V.M., Platonov V.E. J. Fluor. Chem. 2012, 135, 159–166. doi: 10.1016/j.jfluchem.2011.10.006
Malyuta N.G., Platonov V.E., Furin G.G., Yakobson G.G. Tetrahedron 1975, 31, 1201–1207. doi: 10.1016/0040-4020(75)85057-5
Осина О.И., Штейнгарц В.Д. ЖОрХ. 1974, 10, 329–334. [Osina O.I., Shteingarts V.D., C. A. 1974, 80, 120611y).