Journal of the American Chemical Society p. 4824 - 4833 (1981)
Update date:2022-07-31
Topics:
Chae, Woo-Ki
Baughman, Sharon A.
Engel, Paul S.
Bruch, Manfred
Oezmeral, Cenan
et al.
Four acyclic cis 1,2-diazenes, azo-1-adamantane (cis-ada), azo-bicyclo<2.2.2>octane (cis-<2.2.2>), azo-1-bicyclo<2.2.1>heptane (cis-<2.2.1>), and azo-1-bicyclo<2.1.1>hexane (cis-<2.1.1>) have been generated by UV irradiation of the corresponding trans-isomers.These compounds differ greately in stability, cis-<2.1.1> easily surviving at 100 deg C and cis-ada not being isolable.Whereas cis-<2.1.1> and cis-<2.2.1>only isomerize back to trans on heating, the other two compounds undergo competing loss of nitrogen.The observation that the energy of the transition state for isomerization remains at 42 +/- 1 kcal mol-1 regardless of the cis ground state energy is used to argue that thermal isomerization proceeds via semilinearization rather than rotation.A remarkable correlation of cis ground state energy with cis n,?* excitation energy has emerged from this study.
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