Journal of the American Chemical Society p. 3319 - 3325 (1989)
Update date:2022-08-05
Topics:
Baldwin, John E.
Ghatlia, Naresh D.
The relative rates of electrocyclic isomerization of 5,5-dimethylbicyclo<2.1.0>pent-2-ene and the 2-(2)H, 1,2,4-(2)H3, 1,2,3,4-(2)H4, and 1,4-(13)C2 isotopic variants of this system have been determined at 43.6-44.0 deg C.There is no detectable carbon-13 effect; deuterium substitution at C(2) is associated with a small kH/kD effect, 1.02, and a deuterium at C(1) results in a very large effect, 1.26.The kH/kD(d3) effect between 24.6 and 54.7 deg C shows some sensitivity to temperature, ranging from 1.83 to 1.64.The data exclude an important magnetic isotopeeffect on the isomerization and provide no support for a singlet --> triplet intersystem crossing along the reaction coordinate.
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