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Phosphonyl, Phosphonothioyl, Phosphonodithioyl and Phosphonotrithioyl Radicals: Generation and Study of Their Addition onto Alkenes

Chrystel Lopin, Géraldine Gouhier, Arnaud Gautier and Serge R. Piettre*

*Laboratoire des Fonctions Azotées et Oxygénées Complexes, UMR CNRS 6014, IRCOF-Université de Rouen, Rue Tesnières, F-76821 Mont Saint Aignan, France, Email:

C. Lopin, G. Gouhier, A. Gautier, S. R. Piettre, J. Org. Chem., 2003, 68, 9916-9923.

DOI: 10.1021/jo0348064 (free Supporting Information)

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When treated with a radical initiator selenophosphates, selenophosphorodithioates, selenophosphorothioates and selenophosphorotrithioates undergo homolytic cleavage of the P-Se bond to generate radicals. Addition onto electron-rich and electron-poor alkenes in the presence of a hydrogen donor delivers the expected adducts in good yields.

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Radical Chain Process of the Addition Reaction onto Alkenes, TTMSSH: tris(trimethylsilyl)silane

Key Words

thiophosphonates, phosphonates, radical addition, alkenes, tris(trimethylsilyl)silane

ID: J42-Y2003-800