Reaction of Chlorosulfonyl Isocyanate with Fluorosubstituted Alkenes: Evidence of a Concerted Pathway

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• 作者：Dale F. Shellhamer ; Kevyn J. Davenport ; Danielle M. Hassler ; Kelli R. Hickle ; Jacob J. Thorpe ; David J. Vandenbroek ; Victor L. Heasley ; Jerry A. Boatz ; Arnold L. Reingold ; Curtis E. Moore
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：November 19, 2010
• 年：2010
• 卷：75
• 期：22
• 页码：7913-7916
• 全文大小：726K
• 年卷期：v.75,no.22(November 19, 2010)
• ISSN：1520-6904

文摘

Concerted reactions are indicated for the electrophilic addition of chlorosulfonyl isocyanate with monofluoroalkenes. A vinyl fluorine atom on an alkene raises the energy of a stepwise transition state more than the energy of the competing concerted pathway. This energy shift induces CSI to react with monofluoroalkenes by a one-step process. The low reactivity of CSI with monofluoroalkenes, stereospecific reactions, the absence of 2:1 uracil products with neat fluoroalkenes, and quantum chemical calculations support a concerted pathway.