A reexamination of the molecular mechanism of the Diels–Alder reaction between tetrafluoroethene and cyclopentadiene

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• 作者：Radomir Jasiński
• 关键词：Diels–Alder reaction ; DFT study ; Kinetic isotope effects ; Stepwise mechanism
• 刊名：Reaction Kinetics, Mechanisms and Catalysis
• 出版年：2016
• 出版时间：October 2016
• 年：2016
• 卷：119
• 期：1
• 页码：49-57
• 全文大小：491 KB
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Industrial Chemistry and Chemical Engineering
  Physical Chemistry
  
• 出版者：Akad茅miai Kiad贸, co-published with Springer Science+Business Media B.V., Formerly Kluwer Academic
• ISSN：1878-5204
• 卷排序：119

文摘

DFT calculation results shed a new light on the mechanism of cycloaddition reaction between tetrafluoroethene and cyclopentadiene. The unique influence of fluorine atoms on the ethylene derivative molecule causes the [2 + 2] cycloaddition process to take place according to a stepwise, biradical mechanism. At the same time, the competitive and independent path leads to a one-step (and not a two-step, as was once thought) cycloaddition reaction leading to a [2 + 4] cycloadduct.