Use of O,Se-acetals for radical-mediated phenylseleno group transfer reactions

Article abstract of DOI:10.1055/s-1996-4182

Ester substituted O,Se-acetals are very efficient radical precursors which can be used for intermolecular formation of C-C bonds via phenylseleno group transfer. The nucleophilic nature of the radical intermediates has been demonstrated and good yields were obtained with alkenes substituted by electron-withdrawing groups. Interestingly, the slow rate of phenylseleno group transfer permitted addition to nonactivated olefins. An intramolecular variant of this reaction provides a simple and efficient access to tetrahydrofuran derivatives.