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Fragmentation of nitrone triflates to 9-membered rings

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

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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: 17 Jul 2013 11:15
    URI: http://strathprints.strath.ac.uk/id/eprint/35258

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