Monatshefte für Chemie / Chemical Monthly

, Volume 118, Issue 1, pp 115–125 | Cite as

Über Reaktionen mit Betainen, 22. Mitt. Über S-Bétaine und ihre Beziehungen zu stabilen S-Yliden

  • Erich Ziegler
  • Helga Wittmann
  • Heinz Sterk
Organische Chemie Und Biochemie

Reactions with betaines, XXII. On S-betaines and their relationship to the stable S-ylides

Abstract

A comparative study has been performed on ethyl-methyl- and diethyl-mercaptoacetic acid (1 and2), and thianeaceticacid betain (3) with respect to their reactivity towards haloacetic acid anhydrides and 4-nitrobenzene-diazonium tetrafluoroborate. The results show that in analogy to related N-betaines the alkyl substituents at the cationic reaction center display a strong influence on reactivity. The most stable S-ylides are obtained from the cyclic S-betain3 in high yield. The1H-NMR spectra reveal that the protons of the methylene groups in compounds1–3 are fully exchanged for deuterium (in D2O) in contrast to the behavior of the corresponding N-betaines.

Keywords

Tetrahydrothiopyranium acetic acid betain Mono- and diacyl-S-ylides 1,5-Bis (4-nitrophenyl)-3-tetrahydrothiopyranium formazane tetrafluoro-borate 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literatur

  1. [1]
    21. Mitt.:Ziegler E, Wittmann H (1986) Monatsh Chem 117: 653Google Scholar
  2. [2]
    Ziegler E, Wittmann H (1982) Monatsh Chem 113: 723Google Scholar
  3. [3]
    Wittmann H, Ziegler E (1983) Monatsh Chem 114: 1223Google Scholar
  4. [4]
    Wittmann H, Ziegler E, Sterk H, Peters K, Peters EM, v Schnering HG (1985) Monatsh Chem 116: 1189Google Scholar
  5. [5]
    Carrara G (1893) Gazz Chim Ital 23: 496Google Scholar
  6. [6]
    Letts EA (1878) J Chem Soc [London] 1878: 683Google Scholar
  7. [7]
    Corbridge DEC, Lowe EJ (1954) J Chem Soc 1954: 493Google Scholar
  8. [8]
    Ziegler E, Wittmann H (1985) Monatsh Chem 116: 821Google Scholar
  9. [9]
    Wittmann H, Ziegler E, Peters K, Peters EM, v Schnering HG (1983) Monatsh Chem 114: 1097Google Scholar
  10. [10]
    Adams J, Hoffmann L Jr, Trost BM (1970) J Org Chem 35: 1600Google Scholar
  11. [11]
    Johnson AW (1966) Ylid chemistry, Academic Press, New York London, S 321. Dort zitiert:Ingold CK, Jessop JA (1930) J Chem Soc 1930: 713;Johnson AW, Lacount RB (1961) J Amer Chem Soc 83: 417;Hughes ED, Kuriyan KJ (1935) J Chem Soc 1935: 1609Google Scholar
  12. [12]
    Hünig S, Boes O (1953) Liebigs Ann Chem 579: 28Google Scholar
  13. [13]
    Wittmann H, Ziegler E (1982) Monatsh Chem 113: 1451Google Scholar

Copyright information

© Springer-Verlag 1987

Authors and Affiliations

  • Erich Ziegler
    • 1
  • Helga Wittmann
    • 1
  • Heinz Sterk
    • 1
  1. 1.Institut für Organische ChemieKarl-Franzens-Universität GrazGrazÖsterreich

Personalised recommendations