Nasipuri, Dhanonjoy ; Dalal, Ila de (1976) Cyclisation reactions. Part IV. Stereochemistry of cyclialkylation of 2-(2-arylethyl)-1,3,3-trimethylcyclohexyl cations and their equivalents Journal of the Chemical Society, Perkin Transactions 1 (1). pp. 19-22. ISSN 0300-922X
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Official URL: http://www.rsc.org/publishing/journals/P1/article....
Related URL: http://dx.doi.org/10.1039/P19760000019
Abstract
The stereochemistry of cyclialkylation of 2-(2-arylethyl)-1,3,3-trimethylcyclohexyl cations (I), generated from the corresponding 6-alcohols (VIII) has been studied. Whereas kinetically controlled cyclisation gives a preponderance of the trans-podocarpa-8,11,13-trienes (VI) to the extent of 75%, the thermodynamically controlled reaction favours the cis-isomers (V) almost in a reverse ratio. A qualitative estimate of the relative energies of the two isomers supports the greater stability of the cis. The results explain some anomalous reports in the literature.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 27132 |
| Deposited On: | 08 Dec 2010 12:40 |
| Last Modified: | 04 Mar 2011 04:47 |
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