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Free Content Acid-Catalyzed Reactions of N-Methyl-1,2,4-Triazoline-3,5-Dione (MeTAD) with Some Polyaromatic Hydrocarbons

The acid-catalyzed reactions of N-methyl-1,2,4-triazoline-3,5-dione with naphthalene, anthracene, and phenanthrene have been studied using trifluoroacetic acid as catalyst. Quite different results between these reactions were ultimately observed. Reaction with naphthalene appears to be the result of a straightforward acid-catalyzed DA reaction. Reactions with anthracene and phenanthrene, however, are most consistent with formation of carbocation intermediates. The fate of the carbocation, and the nature of the products, depends upon the individual rates of competing inter- and intramolecular reactions.

Keywords: 1-ARYL URAZOLES; DIELS-ALDER CYCLOADDITION; METAD; N-METHYL-1,2,4-TRIAZOLINE-3,5-DIONE; POLYCYCLIC AROMATIC HYDROCARBONS; TRIFLUOROACETIC ACID

Document Type: Research Article

Publication date: 01 March 2013

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  • Advanced Chemistry Letters is an international multidisciplinary peer-reviewed journal covering all fundamental and applied research areas of chemical sciences including organic chemistry, inorganic chemistry, synthetic chemistry, medicinal chemistry, analytical chemistry, organometallic chemistry, nuclear chemistry, electrochemistry, atmospheric chemistry, environmental chemistry, materials chemistry, materials science, supramolecular chemistry, physical chemistry, polymer chemistry, bioinorganic chemistry, physical organic chemistry, surface chemistry, biochemistry, molecular biology, chemical biology, food chemistry, natural product chemistry, neurochemistry, pharmacology, photochemistry, photobiology, toxicology, nanoscience, nanotechnology, agrochemistry, green chemistry, marine chemistry, geochemistry, petrochemistry, radiochemistry, astrochemistry, molecular physics, chemical engineering, quantum chemistry, and theoretical and computational chemistry.
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