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Reaction of an “Invisible” Frustrated N/B Lewis Pair with Dihydrogen

Authors

  • Sina Schwendemann,

    1. Organisch-Chemisches Institut, Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251 8336503
    2. Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602 (Japan)
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  • Shunsuke Oishi,

    1. Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602 (Japan)
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  • Prof. Dr. Susumu Saito,

    1. Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602 (Japan)
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  • Dr. Roland Fröhlich,

    1. Organisch-Chemisches Institut, Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251 8336503
    2. X-Ray crystal structure analyses
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  • Dr. Gerald Kehr,

    1. Organisch-Chemisches Institut, Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251 8336503
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  • Prof. Dr. Gerhard Erker

    Corresponding author
    1. Organisch-Chemisches Institut, Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251 8336503
    • Organisch-Chemisches Institut, Universität Münster, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251 8336503

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Abstract

D-(+)-Camphor forms the enamine 2 with piperidine. Compound 2 adds HB(C6F5)2 at the enamine carbon atom C3 to form a Lewis acid/Lewis base adduct (exo-/endo-isomers of 3). Exposure of 3 to dihydrogen (2.5 bar, room temperature) leads to heterolytic splitting of H2 to form the H+/H addition products (4, two diastereoisomers) of the “invisible” frustrated Lewis pairs (5, two diastereoisomers) that were apparently generated in situ by enamine hydroboration under equilibrium conditions.

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