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The thermal unimolecular isomerization of 1,1-divinylcyclopropane

✍ Scribed by Jorge H. Alonso; William R. Dolbier JR.; Henry M. Frey

Publisher
John Wiley and Sons
Year
1974
Tongue
English
Weight
253 KB
Volume
6
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The thermal isomerization of 1,1‐divinylcyclopropane has been investigated in the gas phase in the temperature range of 238 to 288°C and for pressures in the range of 4 to 12 torr. The isomerization to 1‐vinylcyclopentene is homogeneous and kinetically first order and almost certainly unimolecular. The rate constants yield the Arrhenius equation

or

The assumption of a similar transition state for this isomerization with that of l‐methyl‐l‐vinylcyclopropane leads to a value for an alkylpentadienyl radical stabilisation energy of 19.2 ± 1.6 kcal/mole (80.4 ± 6.7 kJ/mole), and this value is compared with other estimates.

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