Thermal Isomerization of (+)-<i>cis</i>- and (−)-<i>trans</i>-Pinane Leading to (−)-β-Citronellene and (+)-Isocitronellene
作者:Achim Stolle、Bernd Ondruschka、Werner Bonrath、Thomas Netscher、Matthias Findeisen、Markus M. Hoffmann
DOI:10.1002/chem.200800298
日期:2008.7.28
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
萜类化合物的催化和未催化重排反应在精细化学品的实验室和工业规模合成中起主要作用。本文中,我们介绍了pin烷(1)的热诱导异构化反应的结果。在流式反应器中对(+)-顺-(1a)和(-)-反式-ane烷(1b)的热行为的研究表明,与(-)-的形成有关的反应性和选择性都存在显着差异主要产品有β-香茅烯(2)和(+)-异香茅烯(3)。基于反应机理和1a和1b的基态几何结构,讨论了这些结果的可能解释。为了确定由2和3的烯环化引起的副反应,