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Russian Chemical Bulletin

, Volume 59, Issue 8, pp 1668–1670 | Cite as

An unusual reaction of propargylamines with CH2I2 and Et3Al

  • I. R. RamazanovEmail author
  • A. V. Yaroslavova
  • L. M. Khalilov
  • U. M. Dzhemilev
  • O. M. Nefedov
Brief Communications

Abstract

N-{2-[(1-R-Cyclopropyl)methyl]prop-2-enyl}-N,N-dimethylamines were prepared in 80-90% yields by the reaction (5 h, 23-25 C) of propargylamines R-C=C-CH2NMe2 (where R = alkyl, Ph) with a system of reactants CH2I2-Et3Al taken in the molar ratio [propargylamine]: [Et3Al]: [CH2I2] = 1: 6: 6. In the case of phenyl-substituted propargyl- amine, N-({1-[(1-phenylcyclopropyl)methyl]cyclopropyl}methyl)-N,N-dimethylamine is selectively formed in 76% yield upon the elongation of the reaction time to 4 days.

Key words cyclopropanes propargylamines diiodomethane triethylaluminum. 

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Copyright information

© Springer Science+Business Media, Inc.  2010

Authors and Affiliations

  • I. R. Ramazanov
    • 1
    Email author
  • A. V. Yaroslavova
    • 1
  • L. M. Khalilov
    • 1
  • U. M. Dzhemilev
    • 1
  • O. M. Nefedov
    • 2
  1. 1.Institute of Petroleum Chemistry and CatalysisRussian Academy of SciencesUfa, BashkortostanRussian Federation
  2. 2.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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