Cyclopropyl-allyl rearrangement gem-dibromocyclopropanes under the action of aluminum carbenoides

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅或者付费存取

详细

It was found for the first time that 2,3-dialkyl-substituted gem-dibromocyclopropanes react with a solution of aluminum carbenoid Me2AlCH2I in CH2Cl2 to give substituted bromoalkenes in good yield. The reaction is sensitive both to the nature of the organoaluminum Lewis acid and to the nature of the substitution of gem-dibromocyclopropane. A theoretical cyclopropyl-allyl rearrangement has been developed. The B3LYP/6-31G(d) method was used to calculate the free activation energies of the cyclopropyl-allyl rearrangement step for a number of gem-dibromocyclopropanes and aluminum-containing Lewis acids.

作者简介

A. Yaroslavova

Institute of Petrochemistry and Catalysis of Russian Academy of Sciences

prosp. Oktyabrya, 141, Ufa, 450075 Russia

T. Zosim

Institute of Petrochemistry and Catalysis of Russian Academy of Sciences

Email: tania-ygnty@yandex.ru
prosp. Oktyabrya, 141, Ufa, 450075 Russia

I. Ramazanov

Institute of Petrochemistry and Catalysis of Russian Academy of Sciences

prosp. Oktyabrya, 141, Ufa, 450075 Russia

参考

  1. Thankachan A.P., Sindhu K.S., Krishnan K.K. Org. Biomol. Chem. 2015, 13, 8780–802. doi: 10.1039/c5ob01088h
  2. Doering E.W., Hoffmann A.K. J. Am. Chem. Soc. 1954, 76, 6162–6165. doi: 10.1021/ja01652a087
  3. Kostikov R.R., Molcahnov A.P. Top. Curr. Chem. 1990, 155, 41.
  4. Fedoryński M. Chem. Rev. 2003, 103, 1099–1132. doi: 10.1002/chin.200326275
  5. Murphy J.A., Scott K.A., Sinclair R.S., Lewis N. Tetrahedron Lett. 1997, 38, 7295–7298. doi: 10.1016/S0040-4039(97)01695-X
  6. Murphy J.A., Scott K.A., Sinclair R.S., Martin C.G., Kennedy A.R., Lewis N. J. Chem. Soc., Perkin Trans. 1. 2000, 15, 2395–2408. doi: 10.1039/b002565h
  7. Trost B.M., Oslob J.D. J. Am. Chem. Soc. 1999, 121, 13, 3057–3064. doi: 10.1021/ja983617d
  8. Sydnes L.K., Mungaroo R., Aanesen B.A. Acta Chem. Scand. 1998, 52, 1386–1391. doi: 10.3891/acta.chem.scand.52-1386
  9. Banwell M.G., Reum M.E. Advances in Strain in Organic Chemistry. JAI Press. 1991, 1, 19.
  10. Nerdel F., Buddrus J. Tetrahedron Lett. 1965, 6, 3197–3198. doi: 10.1016/S0040-4039(01)89211-X
  11. Skattebоl L., Boulette B. J. Org. Chem. 1966, 31, 81–85. doi: 10.1021/jo01339a016
  12. Ramazanov I.R., Yumagulova A.V., Dzhemilev U.M., Nefedov O.M. Tetrahedron Lett. 2009, 50, 4233–4235. doi: 10.1002/chin.200944057
  13. Kadikova R.N., Ramazanov I.R., Zosim T.P., Yaroslavova A.V., Dzhemilev U.M. Tetrahedron Lett. 2015, 71, 3290–3295. doi: 10.1016/j.tet.2015.03.113
  14. Ramazanov I.R., Yaroslavova A.V., Dzhemilev U.M. Tetrahedron Lett. 2016, 57, 4024–4026. doi: 10.1016/j.tetlet.2016.07.043
  15. Ramazanov I.R., Kadikova R.N., Zosim T.P., Dzhemilev U.M., de Meijere A. Eur. J. Org. Chem. 2017, 47, 7060–7067. doi: 10.1002/ejoc.201700991
  16. Ramazanov I.R., Yaroslavova A.V., Yaubasarov N.R., Dzhemilev U.M. Synlett. 2018, 29, 627–629. doi: 10.1055/s-0036-1591731
  17. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Petersson G.A., Nakatsuji H., Li X., Caricato M., Marenich A. V., Bloino J., Janesko B.G., Gomperts R., Mennucci B., Hratchian H.P., Ortiz J.V., Izmaylov A.F., Sonnenberg J.L., Williams-Young D., Ding F., Lippari- ni F., Egidi F., Goings J., Peng B., Petrone A., Henderson T., Ranasinghe D., Zakrzewski V.G., Gao J., Re- ga N., Zheng G., Liang W., Hada M., Ehara M., Toyo- ta K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Throssell K., Montgomery J.A.Jr., Peralta J.E., Ogliaro F., Bear- park M.J., Heyd J.J., Brothers E.N., Kudin K.N., Sta- roverov V.N., Keith T.A., Kobayashi R., Normand J., Raghavachari K., Rendell A.P., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Millam J.M., Klene M., Adamo C., Cammi R., Ochterski J.W., Martin R.L., Morokuma K., Farkas O., Foresman J.B., Fox D.J. Gaussian 16, Revision B.01. Gaussian, Inc., Wallingford CT, 2016.

补充文件

附件文件
动作
1. JATS XML
下载

版权所有 © Russian Academy of Sciences, 2025