1064210-97-4Relevant academic research and scientific papers
Thermal isomerization of (+)-cis- and (-)-trans-pinane leading to (-)-β-citronellene and (+)-isocitronellene
Stolle, Achim,Ondruschka, Bernd,Bonrath, Werner,Netscher, Thomas,Findeisen, Matthias,Hoffmann, Markus M.
experimental part, p. 6805 - 6814 (2009/08/07)
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- (la) and (-)-trans-pinane (1b) 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 groundstate geometries for 1a and 1b. 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 10H18-hydrocarbon products formed from 1.
