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

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Abstract

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.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    A. P. Molchanov, A. V. Stepakov, V. V. Gurzhii & R. R. Kostikov

  2. Hanoi University of Science and Technology, 1 Dai Co Viet Road, Ha Noi, Viet Nam

    T. Q. Tran

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  1. A. P. Molchanov
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  2. T. Q. Tran
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  3. A. V. Stepakov
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  4. V. V. Gurzhii
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  5. R. R. Kostikov
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Correspondence to A. P. Molchanov.

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Dedicated to the 100th Anniversary of Corresponding Member of the Russian Academy of Sciences A.A. Petrov

Original Russian Text © A.P. Molchanov, T.Q. Tran, A.V. Stepakov, V.V. Gurzhii, R.R. Kostikov, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 4, pp. 547–551.

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Molchanov, A.P., Tran, T.Q., Stepakov, A.V. et al. Methyl (E)-2-(2-phenylcyclopropylidene)acetate: Synthesis, isomerization, and reaction with 1,3-diphenyl-2-benzofuran. Russ J Org Chem 49, 530–535 (2013). https://doi.org/10.1134/S1070428013040064

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  • DOI: https://doi.org/10.1134/S1070428013040064

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