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Synthesis of azodicarboxylic acid imide, its N-substituted derivatives and their use as dienophiles in the Diels-Alder reaction

M. Furdík, S. Mikulášek, M. Livař, and S. Priehradný

Department of Organic Chemistry, Faculty of Natural Sciences, Komenský University, Bratislava


Abstract: A new method of preparation of N-substituted hydrazodicarboxylic acid imides (urazoles) is described, based on the thermic cyclization of the iV,iV'-disubstituted hydrazodicarboxylic acid imides (see Scheme 2). A theoretical explanation is given, why aminolysis of the diethyl hydrazodicarboxylate to the proper diamides does not take place at room and raised temperature (see Scheme 1). The adducts resulting from the Diels—Alder reaction of 2-chloro-buta-l,3-diene and 1,2,3,4-tetrachlorocyclopentadiene with a series of N-substituted hydrazodicarboxylic -acid imides (see Scheme 2), were tested as herbicides, insecticides and combined synergists -and insecticides.

Full paper in Portable Document Format: 216a427.pdf (in Slovak)


Chemical Papers 21 (6) 427–442 (1967)

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