RAS Chemistry & Material ScienceЖурнал органической химии Russian Journal of Organic Chemistry

  • ISSN (Print) 0514-7492
  • ISSN (Online) 3034-6304

Cyclopropyl-Allyl Rearrangement of Gem-Dibromocyclopropanes under the Action of Aluminum Carbenoides

PII
S30346304S0514749225050033-1
DOI
10.7868/S3034630425050033
Publication type
Article
Status
Published
Authors
Volume/ Edition
Volume 61 / Issue number 5
Pages
538-543
Abstract
It was found for the first time that 2,3-dialkyl-substituted gem-dibromocyclopropanes react with a solution of aluminum carbenoid MeAlCHI in CHCl 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.
Keywords
алюминийорганические соединения гем-дибромциклопропаны замещенные бромалкены карбеноиды алюминия квантово-химическое моделирование кислоты Льюиса переходное состояние реакционная способность хлорид алюминия циклопропил-аллильная перегруппировка
Date of publication
10.03.2026
Year of publication
2026
Number of purchasers
0
Views
85

References

  1. 1. Thankachan A.P., Sindhu K.S., Krishnan K.K. Org. Biomol. Chem. 2015, 13, 8780–802. doi10.1039/c5ob01088h
  2. 2. Doering E.W., Hoffmann A.K. J. Am. Chem. Soc. 1954, 76, 6162–6165. doi 10.1021/ja01652a087
  3. 3. Kostikov R.R., Molcahnov A.P. Top. Curr. Chem. 1990, 155, 41.
  4. 4. Fedoryński M. Chem. Rev. 2003, 103, 1099–1132. doi 10.1002/chin.200326275
  5. 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. 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. 7. Trost B.M., Oslob J.D. J. Am. Chem. Soc. 1999, 121, 13, 3057–3064. doi 10.1021/ja983617d
  8. 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. 9. Banwell M.G., Reum M.E. Advances in Strain in Organic Chemistry. JAI Press. 1991, 1, 19.
  10. 10. Nerdel F., Buddrus J. Tetrahedron Lett. 1965, 6, 3197–3198. doi 10.1016/S0040-4039(01)89211-X
  11. 11. Skattebоl L., Boulette B. J. Org. Chem. 1966, 31, 81–85. doi 10.1021/jo01339a016
  12. 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. 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. 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. 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. 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. 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., Lipparini F., Egidi F., Goings J., Peng B., Petrone A., Henderson T., Ranasinghe D., Zakrzewski V.G., Gao J., Rega N., Zheng G., Liang W., Hada M., Ehara M., Toyota 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., Bearpark M.J., Heyd J.J., Brothers E.N., Kudin K.N., Staroverov 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.
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