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Russian Chemical Bulletin

, Volume 42, Issue 1, pp 95–97 | Cite as

Ene-type reaction of trisubstituted monoterpene alkenes with methyl sulfite and thionyl chloride

  • V. A. Dragan
  • A. M. Moiseenkov
Organic Chemistry

Abstract

Trisubstituted methylalkenes react with methyl sulfite at ∼25°C in the presence of BF3 · Et2O in the ene-type fashion to give the corresponding methallyl sulfinates. Such compounds can also be prepared under considerably milder conditions by the Et2AlCl-catalyzed reaction of thionyl chloride with mono- and dienes followed by methanolysis of intermediate alkyl sulfinyl chlorides. These reactions represent a new method for terminal functionalization of linear isoprenoids.

Key words

methyl sulfite thionyl chloride monoterpene alkenes ene-type reaction methyl β-alkenylsulfinates Lewis acids catalytic effect 

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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • V. A. Dragan
    • 1
  • A. M. Moiseenkov
    • 1
  1. 1.N.D.Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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