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

被引：45
|
作者：
Jasinski, Radomir [1 ]
机构：
[1] Cracow Univ Technol, Inst Organ Chem & Technol, Warszawska 24, PL-31155 Krakow, Poland
来源：
REACTION KINETICS MECHANISMS AND CATALYSIS | 2016年 / 119卷 / 01期
关键词：
Diels-Alder reaction; DFT study; Kinetic isotope effects; Stepwise mechanism; QUANTITATIVE CHARACTERIZATION; CYCLOADDITION REACTIONS; STEREOSELECTIVITY; REGIO; LIGHT;
D O I：
10.1007/s11144-016-1038-1
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
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.
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页码：49 / 57
页数：9
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