Primary Adduct, γ‐Ketoketene, and Some Subsequent Products of the Reaction of Methyl 6‐Oxo‐5‐phenyl‐1,3,4‐oxadiazinecarboxylate with Norbornene

Christl, Manfred; Lanzendörfer, Ulrike; Grötsch, Maria M.; Hegmann, Joachim

doi:10.1002/anie.198508861

Cited by 7 publications

References 7 publications

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Cycloadditionen von 1,3,4‐Oxadiazin‐6‐onen (4,5‐Diaza‐α‐pyronen), 9. 6‐Oxo‐5‐phenyl‐1,3,4‐oxadiazin‐2‐carbonsäure‐methylester — Synthese und Reaktionen mit Norbornen, Norbornadien, Cyclopropenen, Cyclobuten und Benzvalen

et al. 1990

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Enol lactones, a$-unsaturated ~ Cycloadditions of 1.3.4-Oxadiazin-6-ones (4.5-Diaza-a-pyrones). 9 'I. -Methyl 6-0xo-5-phenyl-1,3,4-oxadiazin-2-carboxylate -Synthesis and Reactions with Norbornene, Norbornadiene. Cyclopropenes, Cyclobutene. and Benzvalene Methyl 6-oxo-5-phenyl-l,3,4-oxadiazin-2-carboxylate (7) was pene, and cyclobutene were converted by 7 mainly into the prepared by treatment of hydrazone 6 with dicyclohexylcar-oxepin derivatives 15, 17, 18, and the oxocin derivative 19, bodiimide. The reactions of 7 with norbornene and norbor-respectively. Benzvalene and 7 provided the tetracynadiene afforded the Diels-Alder adducts 8 and 9, respectively, clo[3.3.0.02~a.04~6]octan~ne 21. In these reactions, small quantiwhich decomposed in solution at 20°C to give mainly the y-ties of p-lactones were formed, too, which together with the oxoketenes 10 and 12 and small amounts of the p-lactones 11 p-lactones 11 and 13 give evidence for the dihydropyryliumand 13, respectively. The stable y-oxoketenes 10, 12, and the olates 24 as intermediates in the thermal denitrogenation of bis(y-oxoketene) 14 were obtained directly from solutions of 7 the Diels-Alder adducts of 7, e.g. A. 6-Oxo-5-phenyl-l,3,4-oxadiazin-2-carbonsauremethylester (7) Der Weg zu 7 ist dem von Steglich et al.3b,4) Chem.

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Cycloadditionen von 1,3,4‐Oxadiazin‐6‐onen (4,5‐Diaza‐α‐pyronen), 9. 6‐Oxo‐5‐phenyl‐1,3,4‐oxadiazin‐2‐carbonsäure‐methylester — Synthese und Reaktionen mit Norbornen, Norbornadien, Cyclopropenen, Cyclobuten und Benzvalen

et al. 1990

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Cycloadditionen von 6H-1,3,4-Oxadiazin-6-onen (4,5-Diaza-α-pyronen), 10. Reaktionen von Bicyclo[2.1.1] hexenen mit 6H-1,3,4-Oxadiazin-6-onen und dynamische Effekte in einem neungliedrigen, überbrückten, α,β-ungesättigten Enollacton2)

et al. 1991

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Cycloadditionen von 6H‐1,3,4‐Oxadiazin‐6‐onen (4,5‐Diaza‐α1‐pyronen), 12. Dieckmann‐Kondensationen ohne Basen

et al. 1993

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M. Christ1 et al. 797 Cycloadditionen von 6H-1,3,4-Oxadiazin-6-onen (4,5-Diaza-a-pyronen), 12"' 1,2-Cyclopentanedione derivatives J Adipic acid, substituted 2-0x0-dimethyl esters Cycloadditions of 6H-1.3,4-0xadiazin-6-ones (4,5-Diaza-a-pyrones). 12 -Dieckmann Condensations without Bases Prepared by treatment of methyl 6-oxo-5-phenyl-6H-l,3,4-oxadiazine-2-carboxylate (1) with norbornene, norbornadiene, and styrene, respectively, the y-oxoketenes 2, 5, and ? were allowed to react with methanol. Inter alia, the semiacetals 3, 6, and 10 of 1,2-~yclopentanedione derivatives were formed. The identity of 3 has been established by an X-ray structure analysis. The pathway to these compounds seems to be closely related to the mechanism of the Dieckmann condensation. By using [D,]methanol, it has been shown that the semiacetal methoxy group underwent an intramolecular [1,2] migration.Methanol was eliminated from semiacetal 10 by chromatography on silica gel with formation of the enol 11. In addition to 3 and 10, the dimethyl adipates 4 and 9 were observed as the expected methanolysis products of the y-oxoketenes 2 and 7, respectively. The diesters 9 were obtained on a second route from ?. Treatment of ? with trifluoroacetic acid and subsequent hydrolysis gave rise to the monoesters 12, which were converted into the diesters 9 by conventional esterification.

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Primary Adduct, γ‐Ketoketene, and Some Subsequent Products of the Reaction of Methyl 6‐Oxo‐5‐phenyl‐1,3,4‐oxadiazinecarboxylate with Norbornene

Cited by 7 publications

References 7 publications

Cycloadditionen von 1,3,4‐Oxadiazin‐6‐onen (4,5‐Diaza‐α‐pyronen), 9. 6‐Oxo‐5‐phenyl‐1,3,4‐oxadiazin‐2‐carbonsäure‐methylester — Synthese und Reaktionen mit Norbornen, Norbornadien, Cyclopropenen, Cyclobuten und Benzvalen

Cycloadditionen von 1,3,4‐Oxadiazin‐6‐onen (4,5‐Diaza‐α‐pyronen), 9. 6‐Oxo‐5‐phenyl‐1,3,4‐oxadiazin‐2‐carbonsäure‐methylester — Synthese und Reaktionen mit Norbornen, Norbornadien, Cyclopropenen, Cyclobuten und Benzvalen

Cycloadditionen von 6H-1,3,4-Oxadiazin-6-onen (4,5-Diaza-α-pyronen), 10. Reaktionen von Bicyclo[2.1.1] hexenen mit 6H-1,3,4-Oxadiazin-6-onen und dynamische Effekte in einem neungliedrigen, überbrückten, α,β-ungesättigten Enollacton2)

Cycloadditionen von 6H‐1,3,4‐Oxadiazin‐6‐onen (4,5‐Diaza‐α1‐pyronen), 12. Dieckmann‐Kondensationen ohne Basen

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