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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 13
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Original Articles

Surface-Mediated Hydrohalogenation of Isoprene: A Facile Preparation of Prenyl Halides

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Pages 2181-2186 | Received 28 Oct 2002, Published online: 17 Aug 2006
 

Abstract

The reaction of isoprene with SOCl2 (0.5 mol equiv.) or PBr3 (0.4 mol equiv.) or PI3 (0.4 mol equiv.) in the presence of SiO2 at −10°C produced prenyl chloride (82%), or bromide (70%) or iodide (65%), respectively, in less than 30 min reaction time.

Acknowledgments

AMS thanks CNPq for a fellowship. We thank Gabriela F. Mendonça, Francesco Spano, and Milton R. Salles for preparation of PI3. We also thank W. Bruce Kover and Joel Jones Jr. for helpful discussions.

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