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Über Reaktionen mit Betainen, 20. Mitt. Synthesen stabiler S-Ylide

Reactions with betaines, XX. Synthesis of stable S-ylides

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

Thetin (1) and the betain of-Thiolanyl-acetic acid,5 react with the anhydrides of trifluoroacetic acid (TFA) and trichloroacetic acid (TClA), respectively, to give stable diacyl-S-ylides2a,b and6a,b, respectively. In contrast to the corresponding N-betaines,1 and5 react with monochloroacetic anhydride (MClA) under formation of the diacyl-ylid2c from1, and the mixed anhydride of chloroacetic acid and chloroacetylthiolaniummethylid carboxylic acid9 from5. The formation of9 requires the establishment of an equilibrium between S-betain and S-ylid forms. An X-ray analysis has been performed on2a.

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Literatur

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Authors and Affiliations

  1. Institut für Organische Chemie, Karl-Franzens-Universität Graz, A-8010, Graz, Österreich

    Helga Wittmann, Erich Ziegler & Heinz Sterk

  2. Max-Planck-Institut für Festkörperforschung, D-7000, Stuttgart 80, Bundesrepublik Deutschland

    Karl Peters, Eva-Maria Peters & Hans G. v. Schnering

Authors
  1. Helga Wittmann
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  2. Erich Ziegler
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  3. Heinz Sterk
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  4. Karl Peters
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  5. Eva-Maria Peters
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  6. Hans G. v. Schnering
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Herrn Dr. Dr. h.c.Herbert Hönel, Graz, mit besten Wünschen zur Vollendung des 95. Lebensjahres gewidmet.

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Wittmann, H., Ziegler, E., Sterk, H. et al. Über Reaktionen mit Betainen, 20. Mitt. Synthesen stabiler S-Ylide. Monatsh Chem 116, 1189–1198 (1985). https://doi.org/10.1007/BF00811252

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  • DOI: https://doi.org/10.1007/BF00811252

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