NDLI: Thermal Isomerization of (+)-cis- and (−)-trans-Pinane Leading to (−)-β-Citronellene and $(+)-Isocitronellene^{†}$

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Thermal Isomerization of (+)-cis- and (−)-trans-Pinane Leading to (−)-β-Citronellene and $(+)-Isocitronellene^{†}$

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Ondruschka, Bernd Hoffmann, Markus M. Bonrath, Werner Stolle, Achim Netscher, Thomas Findeisen, Matthias
Description	Author Affiliation: Stolle A ( Institute for Technical Chemistry and Environmental Chemistry, Friedrich-Schiller University Jena, Lessingstrasse 12, Jena, Germany.)
Abstract	Catalyzed and uncatalyzed rearrangement reactions of terpenoids play a major role in laboratory and industrial-scale synthesis of fine chemicals. Herein, we present our results on the thermally induced isomerization of pinane (1). Investigation of the thermal behavior of (+)-cis- (1 a) and (−)-trans-pinane (1 b) in a flow-type reactor reveals significant differences in both reactivity and selectivity concerning the formation of (−)-β-citronellene (2) and (+)-isocitronellene (3) as main products. Possible explanations for these results are discussed on the basis of reaction mechanism and ground-state geometries for 1 a and 1 b. To identify side reactions caused from ene cyclizations of 2 and 3, additional pyrolysis experiments were conducted that enabled the identification of almost all compounds in the network of $C_{10}H_{18}-hydrocarbon$ products formed from 1.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	22
Volume Number	14
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2008-01-01
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Monoterpenes Chemical Synthesis Terpenes Chemistry Magnetic Resonance Spectroscopy Mass Spectrometry Stereoisomerism Temperature Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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