Fragmentation of nitrone triflates to 9-membered rings |
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| Authors: | Murphy John A Mahesh Mohan McPheators Gary Anand R Vijaya McGuire Thomas M Carling Robert Kennedy Alan R |
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| Institution: | WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom. john.murphy@strath.ac.uk |
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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. |
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