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Synthesis 1996; 1996(2): 253-258
DOI: 10.1055/s-1996-4182
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Use of O,Se-Acetals for Radical-Mediated Phenylseleno Group Transfer Reactions

Philippe Renaud* , Sokol Abazi
  • *Université de Fribourg, Institut de Chimie Organique, Pérolles, CH-1700 Fribourg, Switzerland, Fax +41(37)299739; E-mail philippe.renaud@unifr.ch
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Publication Date:
31 December 2000 (online)

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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.

radicals - selenium - phenylseleno transfer - α-hydroxy acids

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