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

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E . *5 to the formation of cyanuric acid in 50% yields. If only very mildly alkaline or neutral peroxide is used on uric acid, triuret is a probable intermediate, for both triuret and allantoin (XII) can be found. Both of these compounds are converted to cyanuric acid on further treatment with alkaline peroxide. Furthermore, when the oxidizing agent is NH-CO I NH--CH-NH I + -+ (NH,CONH),CO NH--CNH CO I I NHa CO-NH \ H NH-C- NH 1 ICO COOH 1 CO I I NHa NH, (XIII) HrO,+ Hc H O ~ ~ O H N N \/ OH (111) moderately alkaline hydrogen peroxide, the intermediate allantoic acid (XIII) is isolated&; it can also be converted to (111) with acidic hydrogen peroxide or bromine water.

All the bromide in the tribromide is free bromine and can be titrated as such. Heating the tribromide to 150-160" for four hours in a tube gives 2,4dibromo-~-triazinehydrobromide. The latter can also be prepared directly in 95% yield from (I) with bromine in carbon tetrachloride in a sealed tube at 120-125" for 5 hours. It is a yellow powder which decomposes at 290-300" and is insoluble in nonpolar organic solvents. Reaction with aniline gives 2,4di(pheny1amino)-s-triazine; this shows that two of the bromine atoms are attached to the nucleus of the s-triazine ring.

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. (5) It is probable= that the Rakshits4 report of the preparation of s-triazine by heating diformamide sodium in ether with formamidine hydrochloride is true, but the s-triazine is shown3' to come only from the formamidine hydrochloride.

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