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Secondary α-deuterium kinetic isotope effects in [2+4] cycloaddition of (E)-2-phenylnitroethene to cyclopentadiene

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Abstract

Secondary α-deuterium kinetic isotope effects confirm that [2+4] cycloaddition between (E)-2-phenylnitroethene and cyclopentadiene occurs in concerted manner, on both the pathway leading to 6-endo-phenyl-5-exo-nitronorbornene and the pathway leading to the corresponding 6-exo-phenyl-5-endo-nitro isomer. According to Hammond terminology the transition states on competitive pathways should be considered in terms of symmetrical early states.

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Acknowledgments

Generous allocation of computing time by the regional computer center “Cyfronet” in Cracow (grant MNiI/SGI2800/PK/053/2003) and financial support from the Polish Ministry of Science and Higher Education (grant C2/263/DS/2008) are gratefully acknowledged.

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Authors and Affiliations

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

    Magdalena Kwiatkowska, Radomir Jasiński, Maria Mikulska & Andrzej Barański

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  1. Magdalena Kwiatkowska
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  2. Radomir Jasiński
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  3. Maria Mikulska
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  4. Andrzej Barański
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Correspondence to Radomir Jasiński.

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Kwiatkowska, M., Jasiński, R., Mikulska, M. et al. Secondary α-deuterium kinetic isotope effects in [2+4] cycloaddition of (E)-2-phenylnitroethene to cyclopentadiene. Monatsh Chem 141, 545–548 (2010). https://doi.org/10.1007/s00706-010-0292-6

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  • DOI: https://doi.org/10.1007/s00706-010-0292-6

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