A simple, convenient and expeditious approach to cineol
Corresponding Author
Zorica M. Bugarčić
Department of Chemistry, Faculty of Science, University of Kragujevac, Radoja Domanovića 12, P.O. Box 60, 34 000 Kragujevac, Serbia
Department of Chemistry, Faculty of Science, University of Kragujevac, Radoja Domanovića 12, P.O. Box 60, 34 000 Kragujevac, SerbiaSearch for more papers by this authorJelena D. Dunkić
Department of Chemistry, Faculty of Science, University of Kragujevac, Radoja Domanovića 12, P.O. Box 60, 34 000 Kragujevac, Serbia
Search for more papers by this authorBiljana M. Mojsilović
Department of Chemistry, Faculty of Science, University of Kragujevac, Radoja Domanovića 12, P.O. Box 60, 34 000 Kragujevac, Serbia
Search for more papers by this authorCorresponding Author
Zorica M. Bugarčić
Department of Chemistry, Faculty of Science, University of Kragujevac, Radoja Domanovića 12, P.O. Box 60, 34 000 Kragujevac, Serbia
Department of Chemistry, Faculty of Science, University of Kragujevac, Radoja Domanovića 12, P.O. Box 60, 34 000 Kragujevac, SerbiaSearch for more papers by this authorJelena D. Dunkić
Department of Chemistry, Faculty of Science, University of Kragujevac, Radoja Domanovića 12, P.O. Box 60, 34 000 Kragujevac, Serbia
Search for more papers by this authorBiljana M. Mojsilović
Department of Chemistry, Faculty of Science, University of Kragujevac, Radoja Domanovića 12, P.O. Box 60, 34 000 Kragujevac, Serbia
Search for more papers by this authorAbstract
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 Bu3SnH 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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