Issue 0, 1969

Olefin isomerisation. Part I. Equilibration of octalins related to steroid olefins

Abstract

By use of a basic catalyst, lithium β-aminoethylamide in ethylenediamine–benzene, trans1- and trans2-octalins have been equilibrated at three temperatures, and free energies, enthalpies, and entropies of isomerisation have been deduced. Similar but less precise information has been obtained for the interconversion of the corresponding cis1- and -Δ2-octalins. The thermodynamic data are compared with those resulting from other experimental work on related steroid olefins and with the theoretical predictions of quantitative conformational analysis. For the process trans1- octalin trans2-octalin, as dilute solutions in ethylenediamine–benzene (2 : 1), our best values are ΔH=–0·52 ± 0·06 kcal./mole, ΔS=–0·8 ± 0·3 cal./(deg. mole); for the cis-isomers corresponding estimates are +0·25 ± 0·25 kcal./mole and –0·8 ± 0·7 cal./(deg. mole), respectively.

Article information

Article type
Paper

J. Chem. Soc. B, 1969, 467-471

Olefin isomerisation. Part I. Equilibration of octalins related to steroid olefins

P. Oberhänsli and M. C. Whiting, J. Chem. Soc. B, 1969, 467 DOI: 10.1039/J29690000467

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