A Slippery Slope: Mechanistic Analysis of the Intramolecular Scholl Reaction of Hexaphenylbenzene

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• 作者：Pawel Rempala ; Ji//pubs.acs.org/images/entities/rcaron.gif" border="0">í ; Kroulí ; k ; and Benjamin T. King
• 刊名：Journal of the American Chemical Society
• 出版年：2004
• 出版时间：November 24, 2004
• 年：2004
• 卷：126
• 期：46
• 页码：15002 - 15003
• 全文大小：97K
• 年卷期：v.126,no.46(November 24, 2004)
• ISSN：1520-5126

文摘

DFT calculations support an arenium cation-based mechanism for the Scholl reaction converting hexaphenylbenzene to hexa-peri-benzocoronene. The curve connecting fully benzenoid intermediates on the potential energy diagram is convex. This "slippery slope" provides an explanation for the ease of this cascade Scholl reaction. The calculated reaction coordinate predicts that intermediates will not accumulate; this prediction is verified by experiment.