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On the chemoselectivity of formation of 2-(α-hydroxyalkyl)-2,5-dihydrofurans from allenic diols

✍ Scribed by JoséM. Aurrecoechea; Mónica Solay

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
511 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

The Ag(I)-promoted cyclization of 2.5~pentadiene-1,5diols containing both a ~tiary and a secondary or primary hydroxyl group, has been examined. In general, the reaction displays a preference for cyclixation through the more hindered tertiary hydroxyl group, sometimes to the exclusion of akernative pathways involving secondary or primary carbmol centers.

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The synthesis of 2,5-dihydrofurans from
The synthesis of 2,5-dihydrofurans from α-allenic alcohols
✍ Pierre L. Beaulieu; Veronique M. Morisset; Dennis G. Garratt 📂 Article 📅 1980 🏛 Elsevier Science 🌐 French ⚖ 229 KB

a-Allenic alcohols react rapidly with PhSeCl to produce derivatives of 3-phenylseleno-2,5-dihydrofuran in high yields. The synthesis of heterocycles via the electrophilically-induced cyclization of unsaturated acids,' alcohols, 2 and phenols with areneselenenyl halides or derivatives thereof4 has re