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.
R. L. Jones and C. W. Rees, J. Chem. Soc. C, 1969, 2249 DOI: 10.1039/J39690002249
To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.
If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.
If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.
Read more about how to correctly acknowledge RSC content.
Please wait while we load your content...