伪-Diazo-尾-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation
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- 作者：Roger R. Nani ; Sarah E. Reisman
- 刊名：The Journal of the American Chemical Society
- 出版年：2013
- 出版时间：May 15, 2013
- 年：2013
- 卷：135
- 期：19
- 页码：7304-7311
- 全文大小：502K
- 年卷期：v.135,no.19(May 15, 2013)
- ISSN：1520-5126
文摘
An investigation of the intramolecular cyclopropanation reactions of 伪-diazo-尾-ketonitriles is reported. These studies reveal that 伪-diazo-尾-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor鈥揳cceptor-substituted diazo substrates instead produce mixtures of C鈥揌 insertion and dimerization products. 伪-Diazo-尾-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the 伪-cyano-伪-ketocyclopropane products are demonstrated to serve as substrates for SN2, SN2鈥? and aldehyde cycloaddition reactions.