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Reactions of diazo ketones with activated unsaturated compounds in the presence of gallium trichloride

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Abstract

Diazoacetone reacts with methyl acrylate in the presence of anhydrous GaCl3 to give isomeric methyl 2-acetylcyclopropanecarboxylates rather than pyrazolines obtained from diazo esters or by noncatalytic reactions. In a similar reaction, diazoacetophenone yields methyl 2-benzoylcyclopropanecarboxylates, benzoylmethyl acrylate, and benzoylmethyl 2-benzoylcyclopropanecarboxylate via partial transesterification. Addition of an equimolar amount of GaCl3 to diazoacetone in the system CH2Cl2-HCl-H2O unexpectedly produces 4,5-dimethylfuran-3(2H)-one and 1,1′-oxybis(propan-2-one).

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    R. A. Novikov, Yu. V. Tomilov & O. M. Nefedov

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  1. R. A. Novikov
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  2. Yu. V. Tomilov
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  3. O. M. Nefedov
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Correspondence to Yu. V. Tomilov.

Additional information

On the occasion of the 80th anniversary of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0404–0408, February, 2014.

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Novikov, R.A., Tomilov, Y.V. & Nefedov, O.M. Reactions of diazo ketones with activated unsaturated compounds in the presence of gallium trichloride. Russ Chem Bull 63, 404–408 (2014). https://doi.org/10.1007/s11172-014-0444-7

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  • DOI: https://doi.org/10.1007/s11172-014-0444-7

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