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.
An economic and efficient tetrahydrofuranylation of alcohols, imines and alkynes.
TROISI, Luigino;GRANITO, Catia;RONZINI, Ludovico;ROSATO, FRANCESCA;VIDETTA, Valeria
2010-01-01
Abstract
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.File in questo prodotto:
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