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Intramolecular 1,3-Dipolar Cycloaddition of Geminal Difluoro Azomethine Ylides at Multiple Carbon-Carbon Bonds

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Abstract

N-Alkyl- and N-arylimines derived from o-allyl-, o-allyloxy-, and o-(2-propynyloxy)arenecarbaldehydes react with difluorocarbene to give indeno[1,2-b]pyrrole and chromeno[4,3-b]pyrrole derivatives. The reaction involves intermediate formation of difluoro-substituted azomethine ylides which undergo regio- and stereoselective intramolecular ring closure at the multiple bond.

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Authors and Affiliations

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

    M. S. Novikov, A. F. Khlebnikov, I. V. Voznyi, O. V. Besedina & R. R. Kostikov

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  1. M. S. Novikov
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  2. A. F. Khlebnikov
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  3. I. V. Voznyi
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  4. O. V. Besedina
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  5. R. R. Kostikov
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Dedicated to Full Member of the Russian Academy of Sciences V.I. Minkin on his 70th Anniversary

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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 3, 2005, pp. 372–380.

Original Russian Text Copyright © 2005 by Novikov, Khlebnikov, Voznyi, Besedina, Kostikov.

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Novikov, M.S., Khlebnikov, A.F., Voznyi, I.V. et al. Intramolecular 1,3-Dipolar Cycloaddition of Geminal Difluoro Azomethine Ylides at Multiple Carbon-Carbon Bonds. Russ J Org Chem 41, 361–369 (2005). https://doi.org/10.1007/s11178-005-0171-5

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  • DOI: https://doi.org/10.1007/s11178-005-0171-5

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