Abstract
The enhancements of thermolysis rate of azidobenzene produced by ortho phenylazo, benzoyl and substituents are 21180, 70.0 and 22.8 at 393.2 K (decalin solutions). The same ortho substituents produce much smaller enhancements (169, 8.56 and 10.7 respectively) in the pyrolysis rate of 1-azido-2,4-dibromobenzene. These results are interpreted as steric effects on an electro-cyclic thermolysis mechanism, and are not consistent with the alternative pathway of intramolecular 1,3-dipolar addition which continues to be advocated by Hall and Dolan.
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