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Photoinduced Metalation of Nonactivated C-Cl Bonds with Samarium Diiodide: Synthesis of Alkenes with High (Z)-Selectivity through β-Elimination Reactions

José M. Concellón,* Humberto Rodríguez-Solla, Carmen Simal and Mónica Huerta

*Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, 33006, Oviedo, Spain, Email: jmcguniovi.es

J. M. Concellon, H. Rodriguez-Solla, C. Simal, M. Huerta, Org. Lett., 2005, 7, 5833-5835.

DOI: 10.1021/ol0523392 (free Supporting Information)


Abstract

Samarium diiodide promotes a photoinduced metalation of nonactivated C-Cl bonds of O-acetyl chlorohydrins and a β-elimination which affords alkenes with total or high stereoselectivity.

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A Convenient Samarium-Promoted Synthesis of Aliphatic (E)-Nitroalkenes under Mild Conditions

J. M. Concellón, P. L. Bernad, H. Rodríguez-Solla, C. Concellón, J. Org. Chem., 2007, 72, 5451-5423.


Key Words

syn Eliminations, anti Eliminations, Samarium Diiodide


ID: J54-Y2005-2170