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A simple, convenient and expeditious approach to cineol

✍ Scribed by Zorica M. Bugarčić; Jelena D. Dunkić; Biljana M. Mojsilović

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
50 KB
Volume
15
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

A convenient two‐step protocol preparation of cineol (1‐isopropyl‐4‐methyl‐7‐oxabicyclo[2,2,1]heptane) from α‐terpineol (p‐menth‐1‐en‐8‐ol) is reported. The phenylselenoetherification of α‐terpineol with PhSeX (X = Cl, Br, I) as a key step is described. α‐Terpineol reacts with PhSeX to form the corresponding phenylselenoether in short reaction time and in quantitative yield. A subsequent reduction with Bu~3~SnH to cineol proceeds in high yield (98%) © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:468–470, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20044

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