Fragmentation of nitrone triflates to 9-membered rings

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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 (https://doi.org/10.1021/ol071049d)

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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.

ORCID iDs

Murphy, John A., Mahesh, Mohan, McPheators, Gary, Anand, R. Vijaya, McGuire, Thomas M., Carling, Robert and Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015;
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