at Google ScholarTitle data
Breuning, Matthias ; Häuser, Tobias:
Unprecedented formation of stable ketene-N,O-acetals and their rearrangement under basic conditions.
In: Tetrahedron.
Vol. 63
(2007)
Issue 4
.
- pp. 934-940.
ISSN 0040-4020
DOI: https://doi.org/10.1016/j.tet.2006.11.033
Abstract in another language
Treatment of 2,4-disubstituted glutaryl dichlorides with benzimidic acid ethyl ester hydrochloride in the presence of triethylamine did not give the expected bis(acylbenzimidates), but delivered O-acyl-N-ethoxybenzylidene-ketene-N,O-acetals in good to excellent yields. These compounds, which are stable to moisture and chromatography on silica gel, underwent an unprecedented rearrangement to cyclic enamides under stronger basic conditions. A mechanism for this rearrangement is proposed.
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| Keywords: | Acylimidate; Ketene-N,O-acetal; Rearrangement; Benzimidic acid |
| Institutions of the University: | Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry > Professor Organic Chemistry - Univ.-Prof. Dr. Matthias Breuning Faculties Faculties > Faculty of Biology, Chemistry and Earth Sciences Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry |
| Result of work at the UBT: | No |
| DDC Subjects: | 500 Science > 540 Chemistry |
| Date Deposited: | 11 Jan 2022 14:52 |
| Last Modified: | 11 Jan 2022 14:52 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/68321 |