Russian Journal of Organic Chemistry

, Volume 51, Issue 11, pp 1524–1531 | Cite as

Haloiminolactonization of cyclopentene α,α-dichlorocarboxamides. Tandem rearrangement of iminolactones in epoxylactones

  • Z. R. Valiullina
  • V. A. Akhmet’yanova
  • N. A. Ivanova
  • A. S. Erastov
  • E. S. Meshcheryakova
  • M. S. Miftakhov


Electrophilic cyclization initiated by NBS and I2 of 2,2-dichloro-2-[(1R,5S)- and 2,2-dichloro-2-[(1S,5R)-5-hydroxy-2-cyclopent-2-en-1-yl]-N-[(1R)-1-phenylethyl]acetamides was investigated. Stable under conditions of chromatography on SiO2 bicyclic iminoesters, (2Z,3aS,4S,6S,6aS)-6-bromo-3,3-dichloro- and (2Z,3aS,4S,6S,6aS)-3,3-dichloro-6-iodo-2-{[(1R)-1-phenylethyl]imino}hexahydro-2H-cyclopenta[b]furan-4-ols were isolated and characterized, and a possible version was suggested of their step-by-step recyclization transformations. The halocyclization of carboxamides in water-organic mixtures afforded bicyclic epoxylactones (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-5,5-dichlorohexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones, whose reductive dechlorination proceeded stepwise with successive removal of Cl atoms and led to the formation of (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-hexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones.


Ethyl Acetate Petroleum Ether Phenylethyl Reductive Dechlorination Combine Organic Extract 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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Copyright information

© Pleiades Publishing, Ltd. 2015

Authors and Affiliations

  • Z. R. Valiullina
    • 1
  • V. A. Akhmet’yanova
    • 1
  • N. A. Ivanova
    • 1
  • A. S. Erastov
    • 1
  • E. S. Meshcheryakova
    • 2
  • M. S. Miftakhov
    • 1
  1. 1.Ufa Institute of ChemistryRussian Academy of SciencesUfa, BashkortostanRussia
  2. 2.Institute of Petrochemistry and CatalysisRussian Academy of SciencesUfa, BashkortostanRussia

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