Halomethoxylation of monoterpenes using (dichloroiodo)benzene

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

Research output: Contribution to journalArticle

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

Fingerprint

Monoterpenes
Benzene
Stereoselectivity
Regioselectivity
Halogens
Iodine
Methanol
limonene
3-carene
carvone

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Halomethoxylation of monoterpenes using (dichloroiodo)benzene. / Yusubov, Mehman S.; Drygunova, Larisa Alexandrovna; Tkachev, Alexey V.; Zhdankin, Viktor Vladimirovich.

In: Arkivoc, Vol. 2005, No. 4, 27.05.2005, p. 179-188.

Research output: Contribution to journalArticle

Yusubov, MS, Drygunova, LA, Tkachev, AV & Zhdankin, VV 2005, 'Halomethoxylation of monoterpenes using (dichloroiodo)benzene', Arkivoc, vol. 2005, no. 4, pp. 179-188.
Yusubov, Mehman S. ; Drygunova, Larisa Alexandrovna ; Tkachev, Alexey V. ; Zhdankin, Viktor Vladimirovich. / Halomethoxylation of monoterpenes using (dichloroiodo)benzene. In: Arkivoc. 2005 ; Vol. 2005, No. 4. pp. 179-188.
@article{2c8f9ec6d5354fdc875bd41680642d64,
title = "Halomethoxylation of monoterpenes using (dichloroiodo)benzene",
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.",
keywords = "(Dichloroiodo)benzene, Carene, Carvone, Chloromethoxylation, Iodomethoxylation, Limonene, Monoterpenes, Pinene",
author = "Yusubov, {Mehman S.} and Larisa Alexandrovna Drygunova and Tkachev, {Alexey V.} and Zhdankin, {Viktor Vladimirovich}",
year = "2005",
month = "5",
day = "27",
language = "English",
volume = "2005",
pages = "179--188",
journal = "Arkivoc",
issn = "1424-6376",
publisher = "Arkat USA",
number = "4",

}

TY - JOUR

T1 - Halomethoxylation of monoterpenes using (dichloroiodo)benzene

AU - Yusubov, Mehman S.

AU - Drygunova, Larisa Alexandrovna

AU - Tkachev, Alexey V.

AU - Zhdankin, Viktor Vladimirovich

PY - 2005/5/27

Y1 - 2005/5/27

N2 - 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.

AB - 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.

KW - (Dichloroiodo)benzene

KW - Carene

KW - Carvone

KW - Chloromethoxylation

KW - Iodomethoxylation

KW - Limonene

KW - Monoterpenes

KW - Pinene

UR - http://www.scopus.com/inward/record.url?scp=21744435734&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=21744435734&partnerID=8YFLogxK

M3 - Article

VL - 2005

SP - 179

EP - 188

JO - Arkivoc

JF - Arkivoc

SN - 1424-6376

IS - 4

ER -