Issue 18, 1969

Mechanism of heterocyclic ring expansions. Part IV. Reaction of an imidazole, pyrazole, and 1,2,4-triazole with dichlorocarbene

Abstract

On reaction with dichlorocarbene in basic or neutral conditions, 2,4,5-trimethylimidazole gave 5-chloro-2,4,6-trimethylpyrimidine, and 3,5-dimethyl-1,2,4-triazole gave tris-3,5-dimethyl-1,2,4-triazol-1-ylmethane. In basic conditions 3,4,5-trimethylpyrazole gave 4-dichloromethyl-3,4,5-trimethylpyrazolenine but in neutral conditions it gave four minor products: 4-chloro-3,5,6-trimethylpyridazine, 2-chloro-4,5,6-trimethylpyrimidine, 1-trichlorovinyl-3,4,5-trimethylpyrazole, and tris-3,4,5-trimethylpyrazol-1-ylmethane.

Thus the known reactions of dichlorocarbene with 1H-pyrroles are paralleled and several new reactions are observed. Reasons for the observed product distribution, and possible reaction mechanisms, are proposed.

Article information

Article type
Paper

J. Chem. Soc. C, 1969, 2251-2255

Mechanism of heterocyclic ring expansions. Part IV. Reaction of an imidazole, pyrazole, and 1,2,4-triazole with dichlorocarbene

R. L. Jones and C. W. Rees, J. Chem. Soc. C, 1969, 2251 DOI: 10.1039/J39690002251

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