Calix[4]pyrrole as a Promoter of the CuCl-Catalyzed Reaction of Styrene and Chloramine-T

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• 作者：Hé ; ctor Mart&#xed ; nez-Garc&#xed ; a ; Dolores Morales ; Julio Pé ; rez ; Daniel J. Coady ; Christopher W. Bielawski ; Dustin E. Gross ; Luciano Cuesta ; Manuel Marquez ; Jonathan L. Sessler
• 刊名：Organometallics
• 出版年：2007
• 出版时间：December 17, 2007
• 年：2007
• 卷：26
• 期：26
• 页码：6511 - 6514
• 全文大小：70K
• 年卷期：v.26,no.26(December 17, 2007)
• ISSN：1520-6041

文摘

Calix[4]pyrrole, an easy-to-prepare anion receptor, acts to promote the cuprous chloride-catalyzed aziridination of styrene by the nitrene source chloramine-T in acetonitrile. The mechanism of action is believed to involve incipient anion-receptor interactions involving the calix[4]pyrrole NH protons and the chlorine atom of the CuCl, rather than direct bonding to, and activation of, the chloramine-T. Consistent with this supposition were the findings that (1) the use of calix[4]pyrrole, in combination with CuCl, did promote enhanced reactivity when PhINTs was used as the nitrene source and (2) the presence of calix[4]pyrrole had no effect on the reaction when CuI was used as a catalyst. Decreased yields were also seen with CuCl₂, and no appreciable aziridination product was observed when the calix[4]pyrrole was replaced by an appropriately chosen dipyrromethane control compound. On the other hand, the enhancement effect provided by calix[4]pyrrole proved relatively insensitive to the presence of trace quantities of water.