Journal
TETRAHEDRON LETTERS
Volume 51, Issue 46, Pages 5980-5983Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.09.014
Keywords
Radical reactions; Alcohols; Imines; Alkynes; Tetrahydrofuranylation
Categories
Funding
- MIUR
- University of Salento
- C.I.N.M.P.I.S. (Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi)
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The tetrahydrofuranyl radical, generated by heating tetrahydrofuran in the presence of air and allyl or benzyl chloride, becomes a useful tool in order to transform the hydroxyl functions into ethers, or the C=N double bond into amine, or the C-C triple bond into vinyl derivatives. A radical mechanism is proposed followed by a nucleophilic substitution for the alcohol substrate and a radical addition for the iminic and the acetylenic reactants. (C) 2010 Elsevier Ltd. All rights reserved.
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