"Novel Substituent Orientation in Reimer-Tiemann Reactions of Pyrrole-2" by Kevin M. Smith, Frank W. Bobe et al.

Faculty Publications

Title

Novel Substituent Orientation in Reimer-Tiemann Reactions of Pyrrole-2-carboxylates

Authors

Kevin M. Smith, University of California, Davis
Frank W. Bobe, University of California, Davis
Ohannes M. Minnetian, University of California, Davis
Håkon Hope, University of California, Davis
Michael D. Yanuck, University of California, Davis

Document Type

Article

Publication Date

1-1-1985

Abstract

Reimer-Tiemann formylation reactions (base/CHCl3) on 5-substituted pyrrole-2-carboxylates (1, 6, 8, 9, 11, and 13) afford 2-formylpyrroles (5, 7, 10, 12, and 14) in which the formyl group is situated in the position originally occupied by the carboxylate function, and not, as had been expected, in the 5-unsubstituted site. These observations are confirmed by X-ray crystal structures of compounds 5, 7, and 10 and by nuclear Overhauser enhancement experiments for pyrroles 7, 10, and 14. © 1985, American Chemical Society. All rights reserved.

Publication Source (Journal or Book title)

Journal of Organic Chemistry

First Page

790

Last Page

792

Recommended Citation

Smith, K., Bobe, F., Minnetian, O., Hope, H., & Yanuck, M. (1985). Novel Substituent Orientation in Reimer-Tiemann Reactions of Pyrrole-2-carboxylates. Journal of Organic Chemistry, 50 (6), 790-792. https://doi.org/10.1021/jo00206a012

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