Tetrahedron p. 4621 - 4624 (1987)
Update date:2022-08-04
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Bird, C. W.
Kapili, M.
A range of 2-aryl-1-cyanoindazol-3-ones has been prepared and their thermal rearrangement to the corresponding benzimidazo<2,1-b>quinazolones investigated.Quantitative studies using differential scanning calorimetry have provided rates, energies and entropies of activation.The rates of rearrangement of the 2-(p-substituted-phenyl) compounds are shown to be correlated by the Hammett relationship using ?+ rather than ? substituent constants.In the case of the 2-(2,6-dimethylphenyl) and 2-(2,4,6-trimethylphenyl) compounds rearrangement is accompanied by <1,9> sigmatropic shifts of the obstructing methyl groups.
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