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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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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.