Photochemical and thermal ring-contraction of cyclic hydroxamic acid derivatives.

Cyclic hydroxamic acids can undergo a thermal ring contraction after an in situ triflation. High yields of ring-contraction products are obtained with DBU when the migrating carbon is a methylene, while best results are obtained with Et(3)N for the migration of quaternary carbons. In some cases, the regiochemical outcome of the reaction can be controlled by changing the base. This novel thermal rearrangement complements a similar but photochemical rearrangement of N-mesyloxylactams.

Citation

Simon Pichette, Samuel Aubert-Nicol, Jean Lessard, Claude Spino. Photochemical and thermal ring-contraction of cyclic hydroxamic acid derivatives. The Journal of organic chemistry. 2012 Dec 21;77(24):11216-26

PMID: 23198744

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