Abstract
3.3-Dimethyl-1-phenyl-1.2.4-triazolidine-5-thione (3) is oxidized with HgO or KMnO4 to 2-phenylazo-2-propyl-isothiocyanate (5) which is converted to O-alkyl-N-(2-phenylazo-2-propyl)-thiocarbamates (6) and 3-substituted 1-(2-phenylazo-2-propyl)-thioureas (7). The1H-NMR spectra of the thiono urethanes (6) reveal that at room temperature these compounds exist as a mixture of isomers s-cis-6 and s-trans-6 due to an increased rotational barrier about the thiocarbamide bond (C−N) resulting from its partial double bond character.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literatur
J. Schantl, Mh. Chem.105, 322 (1974).
H. Schildknecht undG. Renner, Ann. Chem.761, 189 (1972).
R. C. Goodwin undJ. R. Bailey, J. Amer. Chem. Soc.46, 2827 (1924).
H. Schildknecht undG. Hatzmann, Angew. Chem.80, 287 (1968).
J. Schantl, Mh. Chem.100, 1479 (1969).
H. Schildknecht undG. Hatzmann, Ann. Chem.724, 226 (1969).
J. Schantl, Mh. Chem.101, 568 (1970).
D. J. Blackstock undD. A. R. Happer, Chem. Comm.1968, 63.
H. Kessler, Angew. Chem.82, 237 (1970); dort weitere Lit.
E. S. Stern undC. J. Timmons, Electronic Absorption Spectroscopy in Organic Chemistry, S. 56 (London: Arnold. 1970)
M. J. Janssen, Rec. Trav. chim. Pays-bas79, 454, 464 (1960).
J. Buckingham undR. D. Guthrie, J. Chem. Soc. (C),1969, 1939.
R. A. Bauman, J. Org. Chem.32, 4129 (1967); vgl. Tetrahedron Letters1971, 419.
J. Ronayne undD. H. Williams, Chem. Comm.1966, 712; J. Chem. Soc. (B),1967, 540.
Author information
Authors and Affiliations
Additional information
Mit 1 Abbildung
Oxidationsprodukte von Arylhydrazon-Verbindungen, 12. Mitt. (11. Mitt.1).
Rights and permissions
About this article
Cite this article
Schanlt, J. Oxidation von 3,3-dimethyl-1-phenyl-1,2,4-triazolidin-5-thion. Monatshefte für Chemie 105, 427–440 (1974). https://doi.org/10.1007/BF00907392
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00907392