Murphy, John A. and Mahesh, Mohan and McPheators, Gary and Anand, R. Vijaya and McGuire, Thomas M. and Carling, Robert and Kennedy, Alan R. (2007) Fragmentation of nitrone triflates to 9-membered rings. Organic Letters, 9 (17). pp. 3233-3236. ISSN 1523-7060
Full text not available in this repository. (Request a copy from the Strathclyde author)Official URL: http://dx.doi.org/10.1021/ol071049d
Abstract
A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.
| Item type: | Article |
|---|---|
| ID code: | 35258 |
| Keywords: | nitrone triflates , cyclization , amides , Chemistry |
| Subjects: | Science > Chemistry |
| Department: | Faculty of Science > Pure and Applied Chemistry Faculty of Engineering > Electronic and Electrical Engineering |
| Related URLs: | |
| Depositing user: | Pure Administrator |
| Date Deposited: | 02 Nov 2011 15:13 |
| Last modified: | 04 Oct 2012 14:03 |
| URI: | http://strathprints.strath.ac.uk/id/eprint/35258 |
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