Russian Journal of Organic Chemistry

, Volume 49, Issue 4, pp 530–535 | Cite as

Methyl (E)-2-(2-phenylcyclopropylidene)acetate: Synthesis, isomerization, and reaction with 1,3-diphenyl-2-benzofuran

  • A. P. Molchanov
  • T. Q. Tran
  • A. V. Stepakov
  • V. V. Gurzhii
  • R. R. Kostikov


Treatment of 3-methyl-2-phenylcycloprop-2-ene-1-carboxylic acid with potassium tert-butoxide induced its isomerization into trans-2-methylidene-3-phenylcyclopropane-1-carboxylic acid which was converted into methyl ester, and heating of the latter for 1 h in toluene gave methyl (E)-2-(2-phenylcyclopropylidene)acetate. Thermal isomerization of methyl (E)-2-(2-phenylcyclopropylidene)acetate on prolonged heating in toluene afforded 5-methoxy-3-methyl-2-phenylfuran, and the reaction with 1,3-diphenyl-2-benzofuran resulted in [4 + 2]-cycloaddition at the exocyclic double bond.


Thermal Isomerization Diazoacetate Acid Versus Exocyclic Double Bond Phenylallene 
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  1. 1.
    Binger, P. and Büch, H.M., Top. Curr. Chem., 1987, vol. 135, p. 77; Goti, A., Cordero, F.M., and Brandi, A., Top. Curr. Chem., 1996, vol. 178, p. 1; Binger, P. and Schmidt, T., Meth. Org. Chem. (Houben-Weyl), vol. E17c, p. 2217; Brandi, A. and Goti, A., Chem. Rev., 1998, vol. 98, p. 589; Brandi, A., Cicchi, C., Cordero, F.M., and Goti, A., Chem. Rev., 2003, vol. 103, p. 1213; Audran, G. and Pellisier, H., Adv. Synth. Catal., 2010, vol. 352, p. 575; Pellisier, H., Tetrahedron, 2010, vol. 66, p. 8341.CrossRefGoogle Scholar
  2. 2.
    Greibrokk, T., Acta Chem. Scand., 1973, vol. 27, p. 3207; Rahman, W. and Kuivila, H.G., J. Org. Chem., 1966, vol. 31, p. 772; Kostikov, R.R., Nagi, Sh.M., and Molchanov, A.P., Zh. Org. Khim., 1983, vol. 19, p. 1437; Molchanov, A.P. and Kostikov, R.R., Zh. Org. Khim., 1988, vol. 24, p. 949.CrossRefGoogle Scholar
  3. 3.
    Kostikov, R.R. and Ioffe, A.I., Zh. Org. Khim., 1970, vol. 6, p. 2630; Kostikov, R.R., Vorob’eva, I.S., and Molchanov, A.P., Zh. Org. Khim., 1983, vol. 19, p. 256; Kostikov, R.R. and Molchanov, A.P., Dokl. Akad. Nauk SSSR, 1979, vol. 246, p. 1377.Google Scholar
  4. 4.
    Huval, C.C. and Singleton, D.A., J. Org. Chem., 1994, vol. 59, p. 2020; Singleton, D.A., Huval, C.C., Church, K.M., and Priestley, E.S., Tetrahedron Lett., 1991, vol. 32, p. 5765.CrossRefGoogle Scholar
  5. 5.
    Creary, X., J. Org. Chem., 1978, vol. 43, p. 1777.CrossRefGoogle Scholar
  6. 6.
    Molchanov, A.P., Noskova, O.V., and Kostikov, R.R., Zh. Org. Khim., 1983, vol. 19, p. 1981.Google Scholar
  7. 7.
    Domnin, I.N., Zhuravleva, E.F., and Pronina, N.V., Zh. Org. Khim., 1978, vol. 14, p. 2323.Google Scholar
  8. 8.
    Ampilogova, N.A., D’yakonov, I.A., and Kostikov, R.R., Zh. Org. Khim., 1966, vol. 2, p. 1898.Google Scholar
  9. 9.
    Gilchrist, T.L. and Rees, C.W., J. Chem. Soc. C, 1968, p. 769.Google Scholar
  10. 10.
    Bonete, P. and Nájera, C., J. Org. Chem., 1994, vol. 59, p. 3202.CrossRefGoogle Scholar
  11. 11.
    D’yakonov, I.A. and Komendantov, M.I., Zh. Obshch. Khim., 1963, vol. 33, p. 2448; D’yakonov, I.A., Komendantov, M.I., and Smirnova, T.S., Zh. Org. Khim., 1969, vol. 5, p. 1742; Zhou, L., Ma, J., Zhang, Y., and Wang, J., Tetrahedron Lett., 2011, vol. 52, p. 5484; Briones, J.F. and Davies, H.M.L., Tetrahedron, 2011, vol. 67, p. 4313.Google Scholar
  12. 12.
    Wiberg, K. and Bonneville, G., Tetrahedron Lett., 1982, vol. 23, p. 5385; Chenier, P.J. and Southard, D.A., Jr., J. Org. Chem., 1990, vol. 55, p. 4333.Google Scholar
  13. 13.
    Hang, X-C., Chen, Q-Y.; and Xiao, J-C., Eur. J. Org. Chem., 2008, p. 1101.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • A. P. Molchanov
    • 1
  • T. Q. Tran
    • 2
  • A. V. Stepakov
    • 1
  • V. V. Gurzhii
    • 1
  • R. R. Kostikov
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Hanoi University of Science and TechnologyHa NoiViet Nam

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