Chemistry of Heterocyclic Compounds: s-Triazines and

Chapter I Cyanuric Acid and Derivatives (pages 17–146):
Chapter II Alkyl(Aryl)?s?Triazines (pages 147–184):
Chapter III Monohydroxy, Hydroxyamino, Dihydroxy?s??Triazines and similar Compounds (pages 185–216):
Chapter IV Monoamino? and Diamino?s??Triazines (pages 217–268):
Chapter V Ammelide, Ammeline and similar Compounds (pages 269–308):
Chapter VI Melamine and Substituted Melamines (pages 309–388):
Chapter VII Isocyanuric Acid and Derivatives (pages 389–422):
Chapter VIII Condensed Ring s?Triazine platforms (pages 423–472):
Chapter IX Hexahydro?s?Triazines (pages 473–544):
Chapter X Hexamethylenetetramine (pages 545–596):
Chapter XI S?Triazaborane and Its Derivatives (pages 597–626):

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Additional resources for Chemistry of Heterocyclic Compounds: s-Triazines and Derivatives, Volume 13

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22. A. Weddige, J. prakt. , (2), 10, 212 (1874). 23. G. Lander, J. Chem. ,83, 411 (1903). 24. E. Bamberger and W. , 25, 534 (1892). 25. C. Grundmann, H. Ulrich and A. , 86, 181 (1953). 26. H. , 42, 803 (1909). 27. L. Hinkel, E. Ayling and J. Beynon, J. Chem. , 1935, 676. 28. E. , 29, 170 (1948) through C L m . Abst~acts,44, 9200 (1949). 29. L. Hinkel and T. Watkins, J . Claern. , 1940,407. 30. L. Hinkel and R. Dunn, J . Clsem. ,1930, 1834. 31. J . Goubeau, E. Jahn, A. Kreutzberger and C. Grundmann, J.

NO HC2H, 3H C -C,Hm ~ 3 H b N ----3 (I) (2) (3) s-Triazine was obtained17 in less than 20% yield from difficultly preparable thioformamide (3). dNH - H S 3 H C S H A+SHCN -----t (I) (3) (4) Most recently, Grundmann described6 the preparation of s-triazine by either thermal or base-catalyzed decomposition of formamidine hydrochloride (4). /AH SHCNH, NHs-+ - SHCN --3 (I) Excellent yields are obtainable by this method. Grundmann has observed that for each one of the last three methods, splitting off the group added to the -CH=NH residue, gives an intermediate in which we can assume the existence of an I0 Introduction activated or polar transition state of hydrocyanic acid of the structure H$=N which spontaneously trimerizes.

Grundmann, J. Phys. ; 58, (1954) 32. C. Grundmann and A. Kreutzberger, J. Am. Chem. , 77, 44 (1955). 33. W. von Ruske, Chem. Tech. Berlin, 6, 489 (1954). 34. J. Rakshit, J. Chem. ,103, 1557 (1913). 35. W. Ruske, Chem. Tech. Berlin, 5, 308 (1953). 36. W. Ruske, Chem. Tech. Bevlan, 5, 368 (1953). 37. C. Grundman, H. Schroeder and W. Ruske. Chem. , 87, 1865 (1954). Chemistry of Heterocyclic Compounds, Volume 13 Edwin M. Smolin, Lorence Rapoport Copyright 0 1959 by Interscience Publishers, Inc. CHAPTER I Cyanuric Acid and Derivatives I.

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