The Cycloaddition of Nitrilimines with 1,2-Dibenzoylethylenes

The cycloaddition of nitrilimines with 1,2-dibenzoylethylenes gave an unexpected 1,3-diaryl-4-benzoylpyrazole and benzoic acid, along with an expected cycloadduct, 1,3-diaryl-4,5-dibenzoyl-2-pyrazoline, and its dehydrogenated product, 1,3-diaryl-4,5-dibenzoylpyrazole. The elimination of the benzoyl group from the pyrazoline followed by dehydrogenation was shown to be the course of the unusual reaction.

[1]  F. Toda,et al.  1,3-Dipolar Cycloadditions of N-(p-Substituted benzylidene) p-Substituted Benzylamine N-Oxides with trans-Bis(p-substituted benzoyl)ethylenes and the Substituent Effects on the Reaction Rates , 1978 .

[2]  R. Huisgen.  1,3-Dipolar cycloadditions. 76. Concerted nature of 1,3-dipolar cycloadditions and the question of diradical intermediates , 1976 .

[3]  R. Stradi,et al.  Preparation of 1-Aryl-4,5- and 5,5-diamino-4,5-dihydropyrazoles and 4- and 5-Amino-1-arylpyrazoles , 1976 .

[4]  C. R. Watts,et al.  Origin of reactivity, regioselectivity, and periselectivity in 1,3-dipolar cycloadditions , 1973 .

[5]  R. G. Mlcetich.  Studies in isoxazole chemistry. IV. Isoxazoles via isoxazolines , 1970 .

[6]  R. Huisgen,et al.  1.3-Dipolare Cycloadditionen, XXX. Substituenteneffekte in den Kernresonanzspektren von 1.3-Diphenyl-Δ2-pyrazolinen und 3-Phenyl-Δ2-isoxazolinen , 1967 .

[7]  R. Huisgen,et al.  1.3‐Dipolare Cycloadditionen, XXVII. Zur Anlagerung des Diphenylnitrilimins an nichtkonjugierte Alkene und Alkine; Sterischer Ablauf, Orientierung un Substituenteneinfluß , 1967 .

[8]  F. Effenberger,et al.  Säureamid‐Reaktionen, XLV. Untersuchungen über die Reaktionsfähigkeit von Formamidinen, Dimethylformamid‐diäthylacetal (Amidacetal) und Bis‐dimethyl‐amino‐methoxy‐methan (Aminalester) , 1964 .

[9]  M. Munk,et al.  Enamines as Dipolarophiles in 1,3-Dipolar Addition Reactions , 1964 .

[10]  R. Huisgen.  Kinetics and Mechanism of 1,3‐Dipolar Cycloadditions , 1963 .

[11]  R. Huisgen.  1,3-Dipolar Cycloadditions. Past and Future† , 1963 .

[12]  R. Huisgen,et al.  Diphenyl-nitrilimin und seine 1.3-dipolaren additionen an alkene und alkine , 1962 .

[13]  J. Sauer,et al.  Ringöffnungen der Azole, VI. Die Thermolyse 2.5‐disubstituierter Tetrazole zu Nitriliminen , 1961 .

[14]  T. Konotsune,et al.  Studies on Acetylenic Compounds. I: Oxidation (i). Oxidation of Acetylenic Alcohols. (1)@@@酸化反応 (i) アセチレン系アルコールの酸化 その1 , 1958 .

[15]  L. P. Kuhn,et al.  A Spectroscopic Study of cis- and trans-Dibenzoylethylenes and Related Compounds , 1950 .

[16]  J. S. Gillespie,et al.  1,4-Reduction of Unsaturated 1,4-Diketones by Lithium Aluminum Hydride1a , 1950 .

[17]  J. S. Gillespie,et al.  Reduction of Unsaturated 1,4-Diketones by Aluminum Isopropoxide1 , 1950 .

[18]  C. E. May,et al.  Concerning Aromatic Acetylenic Carbinols , 1947 .

[19]  L. Smith,et al.  The Action of Aliphatic Diazo Compounds upon α,β-Unsaturated Ketones. II.1cis- and trans-Dibenzoylethylene , 1943 .

[20]  E. Buchner,et al.  Ueber hydrirte Derivate des 4‐Phenylpyrazols und über cis‐1‐Phenyl‐trans‐2. 3‐trimethylendicarbonsäure , 1903 .