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Reaction of fluorochlorocarbene with cyclopentadiene, indene, and their alkyl derivatives by phase transfer catalysis

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

Fluorohalocarbene, generated from CHCl2F using phase transfer catalysis, reacts with indene, cyclopentadiene, and their alkyl derivatives to form 2-fluoronaphthalenes or fluorobenzenes in 9–60% yield. Reactions proceed through formation of unstable fluorochlorocyclopropanes, which rearrange selectively independently of their stereochemical configuration into the corresponding aromatic fluorides with elimination of HCl.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    N. V. Volchkov, A. V. Zabolotskikh, A. V. Ignatenko & O. M. Nefedov

Authors
  1. N. V. Volchkov
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  2. A. V. Zabolotskikh
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  3. A. V. Ignatenko
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  4. O. M. Nefedov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1609–1613, July, 1990.

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Volchkov, N.V., Zabolotskikh, A.V., Ignatenko, A.V. et al. Reaction of fluorochlorocarbene with cyclopentadiene, indene, and their alkyl derivatives by phase transfer catalysis. Russ Chem Bull 39, 1458–1461 (1990). https://doi.org/10.1007/BF00957859

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  • DOI: https://doi.org/10.1007/BF00957859

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