Mechanistic, Model Compound, Copolymerization And Modification Reaction Studies of the 4-Substituted-1,2,4-Triazoline-3,5-Dione Ring System

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Mechanistic, Model Compound, Copolymerization And Modification Reaction Studies of the 4-Substituted-1,2,4-Triazoline-3,5-Dione Ring System
Williams, Arthur Grady
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The reaction was complete in approximately 15 minutes. During rotoevaporation , crystals fell out of the warm solution.
These were dried and gave a melting point of 150-5 C. Further drying in pistol at 0.03 mm Hg. and 136 C resulted in decomposition of the solid. A second set of crystals (0.42 g, 97 24%) fell from the original solution. These were dried at 35 in a vacuum oven and gave a melting point of 152-4° (32) .
Infrared absorbances were found at (KBr) 3100 (b), 2850 (sh), 1780 (s), 1700 (
...s), 1660 (s), 1610 (s), 1500 (s), 1400 (s), 1320 (s), 1260 (w), 1220 (s), 1185 (s), 1140 (w) , 1085 (w) , 1060 (s), 1000 (w), 800 (b), 770 (w) , 700 (b) and 630 (w) cm" 1 , NMR signals were found at (Acetone-dg) 1.256 (T), 1.36 (T), 2.16(s), 2.456 (s), 4.256 (Q), 4.306 (Q), 5-66 (s), 7-456 (s), 12.36 (s, broad, existed as 75% enolized tautomer In this solvent). Molecular ion: 302 m/e .
Anal. Calcd. for C^H^N-0 : C, 55-08; H, 4.92; N, 13-77- Pound: C, 55-06; H, 4.94; N, 13-82.
E thy 1-1 , 2-(bis-2-hydro-4-phenyl-l ,2,4-triazoline-3, 5-dionyl )- 3-one-butyrate , 33 .


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