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J Mol Graph Model. 2017 Aug;75:55-61. doi: 10.1016/j.jmgm.2017.04.008. Epub 2017 Apr 27.

One-step versus two-step mechanism of Diels-Alder reaction of 1-chloro-1-nitroethene with cyclopentadiene and furan.

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Cracow University of Technology, Institute of Organic Chemistry and Technology, Warszawska 24, 31-155 Cracow, Poland. Electronic address:


DFT computational study shows that Diels-Alder (DA) reactions of 1-chloro-1-nitroethene with cyclopentadiene and furan have polar nature. However, their mechanism is substantially different. In particular, 1-chloro-1-nitroethene react with cyclopentadiene according to one-step mechanism. In the same time, more favourable channel associated with the P-DA reaction between furan and 1-chloro-1-nitroethene is a domino process, that comprises an initial hetero-Diels-Alder reaction yielding a [2+4] cycloadduct, which experiences a subsequent [3,3] sigmatropic shift to yield the expected formal [4+2] cycloadduct. This is a consequence of more polar nature of reaction, due to higher nucleophilicity of furan in comparison to cyclopentadiene.


DFT study; Diels-Alder reaction; Mechanism; Nitroalkenes

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