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Open Access research with a European policy impact...

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EPRC is a leading institute in Europe for comparative research on public policy, with a particular focus on regional development policies. Spanning 30 European countries, EPRC research programmes have a strong emphasis on applied research and knowledge exchange, including the provision of policy advice to EU institutions and national and sub-national government authorities throughout Europe.

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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.