An expedient construction of seven-membered rings adjoining aromatic systems

T. Kaoudi (1) , Béatrice Quiclet-Sire (1) , S. Seguin (1) , Samir Z. Zard (1, 2)

1 ICSN - Institut de Chimie des Substances Naturelles
2 DCSO - Laboratoire de synthèse organique

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.

Domains: Chemical Sciences; Organic chemistry

T. Kaoudi, Béatrice Quiclet-Sire, S. Seguin, Samir Z. Zard. An expedient construction of seven-membered rings adjoining aromatic systems. Angewandte Chemie International Edition, 2000, 39 (4), pp.731-733. ⟨10.1002/(SICI)1521-3773(20000218)39:4<731::AID-ANIE731>3.0.CO;2-U⟩. ⟨hal-00954900⟩