Monatshefte für Chemie / Chemical Monthly

, Volume 110, Issue 6, pp 1345–1355 | Cite as

Über die Reaktionen von 2-Cyclohexenonen mit Ammoniumthiocyanat bzw. Thioharnstoff Über Heterocyclen, 59. Mitteilung

  • Winfried Wendelin
  • Wolfgang Kern
Organische Chemie und Biochemie

The reactions of 2-cyclohexenones with ammoniumthiocyanate and thiourea

Abstract

The 2-cyclohexenones1 a, b andc react with NH4SCN to give 3,5,5-trimethyl-, 3-methyl-5-phenyl- and 3-methyl-2-cyclohexeniminiumthiocyanates8 a, b andc resp. (i.e. salts of α,β-unsaturated imines) and not the expected diazabicyclononane-thiones5 a, b andc. Alternative formulae for the1—NH4SCN-condensates are discussed and rejected on the basis of IR- and NMR-spectra and the chemical properties of5 a-c.

By action of thiourea inMeOH/NaOMe the 2-cyclohexenones1a, d ande are transformed into 1-hydroxy-5,7,7-trimethyl-, 1-hydroxy-5-methyl- and 1-hydroxy-2,4-diazabicyclo[3.3.1]nonane-3-thiones5 a, d ande resp. The structure of the diazabicyclononane-thiones5 a, d ande is established by means of NMR-, IR- and MS-spectra.

8 a-c and5 e showed no significant herbicidal and only small fungicidal (8 b, c) and insecticidal (8 a-c) activities in screening tests.

Keywords

2-Cyclohexeniminium thiocyanates 2-Cyclohexenones, reactions with thiocyanate and thiourea 2,4-Diazabicyclo[3.3.1]nonane-3-thiones 2-Pyrimidinthiones, bicyclic 

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Copyright information

© Springer-Verlag 1979

Authors and Affiliations

  • Winfried Wendelin
    • 1
  • Wolfgang Kern
    • 1
  1. 1.Institut für Pharmazeutische ChemieUniversität GrazGrazÖsterreich

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