Halomethoxylation of monoterpenes using (dichloroiodo)benzene

Mehman S. Yusubov, Larisa Alexandrovna Drygunova, Alexey V. Tkachev, Viktor Vladimirovich Zhdankin

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

Reactions of (dichloroiodo)benzene or (dichloroiodo)benzene/iodine with various monoterpenes in methanol provide a selective approach to the respective products of chloromethoxylation or iodomethoxylation of the double bond. The halomethoxylation of (+)-3-carene, carvone, and β-pinene proceeds with especially high regio- and stereoselectivity affording an appropriate single product in each case, while the reaction of limonene gives products of functionalization of both double bonds. This new methodology for the controlled introduction of halogen substituents into the structure of naturally occuring monoterpenes provides an entry into various potentially important synthetic intermediates.

Original languageEnglish
Pages (from-to)179-188
Number of pages10
JournalArkivoc
Volume2005
Issue number4
Publication statusPublished - 27 May 2005

Keywords

  • (Dichloroiodo)benzene
  • Carene
  • Carvone
  • Chloromethoxylation
  • Iodomethoxylation
  • Limonene
  • Monoterpenes
  • Pinene

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Halomethoxylation of monoterpenes using (dichloroiodo)benzene'. Together they form a unique fingerprint.

Cite this