Stereochemistry of Nucleophilic Substitution at Cyclo-propanediazonium Ions

Authors

  • Prof. Dr. Wolfgang Kirmse,

    Corresponding author
    1. Abteilung für Chemie der Universität, Postfach 10 21 48, D-4630 Bochum 1 (Germany)
    • Abteilung für Chemie der Universität, Postfach 102148, D-4630 Bochum 1 (Germany)
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  • Dr. Theodor Engbert

    1. Abteilung für Chemie der Universität, Postfach 10 21 48, D-4630 Bochum 1 (Germany)
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Abstract

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Model studies on SN2 substitution in cyclopropanes show that inversion occurs in the “normal case”—at least in compunds having N2 as leaving group. Thus, (1) reacts with configurational inversion to give (2) (4%) alongside the allyl compound (3). The reason for the retention observed in special cases, e.g. on deamination of (4), is probably a partly opened cation such as (5).

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