Journal
CHEMISTRY & BIODIVERSITY
Volume 5, Issue 6, Pages 910-919Publisher
WILEY-BLACKWELL
DOI: 10.1002/cbdv.200890104
Keywords
-
Ask authors/readers for more resources
alpha-Pinene and beta-pinene are abundantly represented in nature; they are obtained from renewable sources and are irreplaceable synthons for commercial-scale production of other terpenes. In a well-known process practiced by Millennium Specialty Chemicals (MSC), hydrogenation of pinenes gives cis- and trans-pinanes, which are oxidized to hydroperoxides, whose reduction gives cis- and trans-pinanols, respectively. Pyrolysis of the pinanols gives linalool. Industrial availability of the pinanols makes them attractive objects for further synthetic research. We found that, in a very simple process of 'chlorooxidation', cis- and trans-pinanols react with hypochloric acid producing a novel chloroketone 1-[3-(2-chloroethyl)-2,2-dimethylcyclobutyl]ethanone and a tricyclic ether 6,9-dimethyl-7-oxatricyclo[4.3.0.0(3,9)]nonane, respectively. Both compounds offer new broad synthetic opportunities, providing access to numerous dimethylcyclobutane derivatives and to C(9)-functionalized pinenes and pinanes. The chlorooxidation reaction was also extended to other terpene alcohols such as dihydroplinol, tetrahydromyrcenol, and tetrahydrolinalool. This review, based on a presentation at the RSC/SCI conference Flavours & Fragrances 2007 in London, September 24 - 26, 2007, will touch on environmental issues related to pinenes, give a brief overview of the existing pinene-based technologies, and discuss the new experimental results.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available