Tetrahedron p. 4621 - 4632 (1985)
Update date:2022-07-30
Topics:
L'Abbe, Gerrit
Stappen, Peter van
Toppet, Suzanne
5-Azido-4-methoxycarbonyl-1-phenyl-1,2,3-triazole (8a) and its phenyl substituted derivatives 8b, c rearrange at 60-80 deg C to give tetrazolyldiazoacetates 9, which have been isolated.When the reactions are allowed to go to completion, products derived from the diazo compounds are obtained; i. e. norcaradienes (10) from benzene solutions and imidazotetrazoles (12) from nitrile solutions.The latter decompose photochemically into diazacyclopentadienonimines (13).A kinetic study of the rearrangement 8 <*> 9 has been carried out and the mechanism (Scheme VI) is discussed in comparison with the Dimroth rearrangement.
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