Rearrangement during cyclisation of some 3-(2-pyrrolyl) propionic acids and related compounds |
| |
Authors: | Michael H. Palmer David S. Leitch Colin W. Greenhalgh |
| |
Affiliation: | Deparment of Chemistry, University of Edinburgh, West Mains Road, Edinburgh EH9 3JJ, Scotland;I.C.I., Organics Division, Manchester M9 3DA, England |
| |
Abstract: | Cyclisation of the title compounds leads to mixtures of the expected 4H-cyclopental[b]pyrrol-4-ones (1), the corresponding 6-ones (3) by a single rearrangement, and the cyclopenta[c]pyrrol-4-ones (4) by a double rearrangement, the proportions depending upon the substituents.The 1H NMR spectra of 2-methyl-4H-cyctopenta[b]thiophen-6-one (3f) shows 6J long range coupling, but this is absent in the corresponding pyrroles (3c,d). The 13C spectra of 1 and 3 cannot be interpreted on the basis of substituent chemical shifts in pyrroles and thiophens, and are clearly -CH = CH-X (X = NMe, NPh, S) bridged derivatives of cyclopent-2-enone. |
| |
Keywords: | Present address: Imperial Chemical Industries Ltd. Organic Division Manchester M9 3DA England. |
本文献已被 ScienceDirect 等数据库收录! |
|