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4-Phenyl-1,2,4-triazole-3,5-dione : ウィキペディア英語版 | 4-Phenyl-1,2,4-triazole-3,5-dione
|Section2= |Section7= |Section8= }} 4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) is an azodicarbonyl compound. PTAD is one of the strongest dienophiles and reacts rapidly with dienes in Diels-Alder reactions. The most prominent use of PTAD was the first successful synthesis of prismane in 1973. ==Synthesis== The compound was first synthesized in 1894 by Johannes Thiele and O. Stange. The oxidation of 4-Phenylurazol with lead tetroxide in sulfuric acid yielded small quantities of the substance. It took until 1971 when a practical synthesis was published. The synthesis starts from hydrazine and diethyl carbonate. The product of this step is reacted with phenyl isocyanate and subsequently transformed to the 4-Phenylurazol. Cyclization and subsequent oxidation yields PTAD (6).
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