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Issue 18, 1969
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Mechanism of heterocyclic ring expansions. Part III. Reaction of pyrroles with dichlorocarbene

Abstract

2,5-Dimethyl-, 2,3,4,5-tetramethyl-, and 3,4-dimethyl-2,5-diphenyl-1H-pyrrole react with dichlorocarbene in basic solution to give 2-dichloromethyl-2H-pyrrole and 3-chloropyridines in low yield. However, in neutral aprotic solution high yields of 3-chloropyridines are formed in a synthetically useful reaction; 2H-pyrroles are not formed.

These results support earlier mechanistic proposals.

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Article type: Paper
DOI: 10.1039/J39690002249
Citation: J. Chem. Soc. C, 1969,0, 2249-2251
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    Mechanism of heterocyclic ring expansions. Part III. Reaction of pyrroles with dichlorocarbene

    R. L. Jones and C. W. Rees, J. Chem. Soc. C, 1969, 0, 2249
    DOI: 10.1039/J39690002249

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