An expedient construction of seven-membered rings adjoining aromatic systems

Talbi Kaoudi; Béatrice Quiclet-Sire; Stéphanie Seguin; Samir Z. Zard

doi:10.1002/(SICI)1521-3773(20000218)39:4<731::AID-ANIE731>3.0.CO;2-U

An expedient construction of seven-membered rings adjoining aromatic systems

Talbi Kaoudi
, Béatrice Quiclet-Sire
, Stéphanie Seguin
, Samir Z. Zard

Institut de Chimie des Substances Naturelles
Laboratoire de Synthèse Organique

Research output: Contribution to journal › Article › peer-review

Abstract

An unusual radical-mediated fusion of a seven-membered ring onto an aromatic system exploits the relatively long lifetime of radicals generated using dithiocarbonares (xanthates). This type of annelation (an example is shown), which was hitherto very difficult to accomplish by more traditional radical methods, was used to construct a variety of complex structures. Y = OAc, CN, (CH₂)₈OAc, CH₂CO₂Et, phthaloyl.

Original language	English
Pages (from-to)	731-733
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	39
Issue number	4
DOIs	https://doi.org/10.1002/(SICI)1521-3773(20000218)39:4<731::AID-ANIE731>3.0.CO;2-U
Publication status	Published - 18 Feb 2000
Externally published	Yes

Keywords

Annulations
C-C coupling
Radical reactions
Xanthates

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10.1002/(SICI)1521-3773(20000218)39:4<731::AID-ANIE731>3.0.CO;2-U

Cite this

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AU - Kaoudi, Talbi

AU - Quiclet-Sire, Béatrice

AU - Seguin, Stéphanie

AU - Zard, Samir Z.

PY - 2000/2/18

Y1 - 2000/2/18

N2 - An unusual radical-mediated fusion of a seven-membered ring onto an aromatic system exploits the relatively long lifetime of radicals generated using dithiocarbonares (xanthates). This type of annelation (an example is shown), which was hitherto very difficult to accomplish by more traditional radical methods, was used to construct a variety of complex structures. Y = OAc, CN, (CH2)8OAc, CH2CO2Et, phthaloyl.

AB - An unusual radical-mediated fusion of a seven-membered ring onto an aromatic system exploits the relatively long lifetime of radicals generated using dithiocarbonares (xanthates). This type of annelation (an example is shown), which was hitherto very difficult to accomplish by more traditional radical methods, was used to construct a variety of complex structures. Y = OAc, CN, (CH2)8OAc, CH2CO2Et, phthaloyl.

KW - Annulations

KW - C-C coupling

KW - Radical reactions

KW - Xanthates

UR - https://www.scopus.com/pages/publications/0034681473

U2 - 10.1002/(SICI)1521-3773(20000218)39:4<731::AID-ANIE731>3.0.CO;2-U

DO - 10.1002/(SICI)1521-3773(20000218)39:4<731::AID-ANIE731>3.0.CO;2-U

M3 - Article

AN - SCOPUS:0034681473

SN - 1433-7851

VL - 39

SP - 731

EP - 733

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 4

ER -

An expedient construction of seven-membered rings adjoining aromatic systems

Abstract

Keywords

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