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Studies on the thermal decarboxylation of 1‐alkoxycarbonylbenzotriazoles
Author(s) -
Katritzky Alan R.,
Zhang GuiFen,
Fan WeiQiang,
Wu Jing,
Pernak Juliusz
Publication year - 1993
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610061007
Subject(s) - decarboxylation , chemistry , thermal decomposition , intermolecular force , carbon dioxide , decomposition , thermal , medicinal chemistry , organic chemistry , photochemistry , catalysis , molecule , thermodynamics , physics
1‐Alkoxycarbonylbenzotriazoles on thermolysis lose carbon dioxide; the decarboxylation is accompanied by the formation of a mixture of 1‐ and 2‐alkylbenzotriazoles, with the N ‐1 isomer predominating over the N ‐2 isomer in all cases. A cross‐over experiment, in which heating equimolar amounts of 1‐benzyloxycarbonylbenzotriazole and 1‐(4‐methylbenzyloxycarbonyl)‐5,6‐dimethylbenzotriazole gave almost all the cross‐over products, supports the proposed intermolecular mechanism for this decarboxylation and the formation of 1‐ and 2‐alkylbenzotriazoles. No decarboxylation was observed for 1‐phenoxycarbonylbenzotriazole.