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Alkylation of sterically hindered 1,3-diketones under phase-transfer conditions

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Sterically hindered 1,3-diketones react selectively with propargyl and allyl bromides under conditions of phase transfer catalysis to giveC-alkylated products, whereas reactions with butyl and benzyl chlorides yield mixtures ofC- andO-isomers. An increase in the size of the substituents present in the initial 1,3-diketone hampers introduction of the second propargyl group. The propargyl-substituted 1,3-diketones undergo cyclization under the alkylation conditions to give substituted furans.

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Authors and Affiliations

  1. Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 3 ul. Institutskaya, 630090, Novosibirsk, Russian Federation

    A. S. Zanina, S. I. Shergina, I. E. Sokolov & M. S. Shvartsberg

Authors
  1. A. S. Zanina
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  2. S. I. Shergina
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  3. I. E. Sokolov
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  4. M. S. Shvartsberg
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Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2518–2521, October, 1996.

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Zanina, A.S., Shergina, S.I., Sokolov, I.E. et al. Alkylation of sterically hindered 1,3-diketones under phase-transfer conditions. Russ Chem Bull 45, 2389–2392 (1996). https://doi.org/10.1007/BF01435389

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  • DOI: https://doi.org/10.1007/BF01435389

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