Issue 1, 1976
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Cyclisation reactions. Part IV. Stereochemistry of cyclialkylation of 2-(2-arylethyl)-1,3,3-trimethylcyclohexyl cations and their equivalents

Dhanonjoy Nasipuri  and  (Miss)Ila de Dalal  

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.

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Article information

DOI
https://doi.org/10.1039/P19760000019
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1976, 19-22

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Cyclisation reactions. Part IV. Stereochemistry of cyclialkylation of 2-(2-arylethyl)-1,3,3-trimethylcyclohexyl cations and their equivalents

D. Nasipuri and I. de Dalal, J. Chem. Soc., Perkin Trans. 1, 1976, 19 DOI: 10.1039/P19760000019

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