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Stepwise, zwitterionic course of hetero-Diels–Alder reaction between 1,2,4-triazine molecular systems and 2-cyclopropylidene-1,3-dimethylimidazoline

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Chemistry of Heterocyclic Compounds Aims and scope

The computational wb97xd/6-311+G(d)(PCM) study confirms without any doubt the polar, stepwise mechanism of hetero-Diels–Alder reactions as illustrated on the example of 5,6-diphenyl-1,2,4-triazine and 2-cyclopropylidene-1,3-dimethylimidazoline. The first reaction stage is the formation of a prereaction molecular complex, which can next convert to two possible zwitterionic intermediates characterized by “cyclic” and “extended” conformation. The first one cyclizes in the second reaction step to the expected six-membered cycloadduct.

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Authors and Affiliations

  1. Cracow University of Technology, Department of Organic Chemistry and Technology, 24 Warszawska St., 31-155, Cracow, Poland

    Radomir Jasiński

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  1. Radomir Jasiński
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Correspondence to Radomir Jasiński.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(4/5), 260–262

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Jasiński, R. Stepwise, zwitterionic course of hetero-Diels–Alder reaction between 1,2,4-triazine molecular systems and 2-cyclopropylidene-1,3-dimethylimidazoline. Chem Heterocycl Comp 58, 260–262 (2022). https://doi.org/10.1007/s10593-022-03081-y

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  • DOI: https://doi.org/10.1007/s10593-022-03081-y

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