Photochemical and Thermal Ring-Contraction of Cyclic Hydroxamic Acid Derivatives
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- 作者：Simon Pichette ; Samuel Aubert-Nicol ; Jean Lessard ; Claude Spino
- 刊名：The Journal of Organic Chemistry
- 出版年：2012
- 出版时间：December 21, 2012
- 年：2012
- 卷：77
- 期：24
- 页码：11216-11226
- 全文大小：582K
- 年卷期：v.77,no.24(December 21, 2012)
- ISSN：1520-6904
文摘
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 Et3N 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.