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In-Flight Epimerization of a Bis-Tröger Base

Authors

  • Ágnes Révész,

    1. Institute of Organic Chemistry and Biochemistry, Flemingovo náměstí 2, 16610 Prague 6 (Czech Republic), Fax: (+420) 220-183-462
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  • Dr. Detlef Schröder,

    Corresponding author
    1. Institute of Organic Chemistry and Biochemistry, Flemingovo náměstí 2, 16610 Prague 6 (Czech Republic), Fax: (+420) 220-183-462
    • Institute of Organic Chemistry and Biochemistry, Flemingovo náměstí 2, 16610 Prague 6 (Czech Republic), Fax: (+420) 220-183-462
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  • Dr. Tibor András Rokob,

    1. Institute of Organic Chemistry and Biochemistry, Flemingovo náměstí 2, 16610 Prague 6 (Czech Republic), Fax: (+420) 220-183-462
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  • Dr. Martin Havlík,

    1. Department of Analytical Chemistry, Institute of Chemical Technology Prague, Technická 5, 16628 Prague 6 (Czech Republic)
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  • Dr. Bohumil Dolenský

    1. Department of Analytical Chemistry, Institute of Chemical Technology Prague, Technická 5, 16628 Prague 6 (Czech Republic)
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  • This work was supported by the Academy of Sciences of the Czech Republic (Z40550506), the European Research Council (AdG HORIZOMS), the Grant Agency of the Czech Republic (203/08/1445), and the Ministry of Education, Youth and Sports of the Czech Republic (MSM 6046137307 and LC 521).

Abstract

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Increased mobility is observed for the sodiated syn and anti isomers of bis-Tröger base 1 relative to that of the protonated variants. Ion-mobility measurements further demonstrate that the pseudo-epimerization of the bis-Tröger base proceeds by a proton-mediated ring opening rather than a retro-Diels–Alder sequence.

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