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• W2023592837 abstract "2,4,6-Trimethylbenzonitriloxid, Benzonitriloxid und Knallsäure ergaben mit Benzvalen (1) in hohen Ausbeuten die Δ2-Isoxazoline 2a – c. Durch Konkurrenzexperimente wurde das Verhältnis der Geschwindigkeitskonstanten der Additionen von Benzonitriloxid an 1 und Norbornen kBenzvalen/kNorbornen ≈ 1 bestimmt. Das Knallsäure-Addukt 2c ließ sich in der folgenden einfachen Reaktionssequenz in Benzvalen-3-carbonitril (4) umwandeln: Ringöffnung durch Natrium-methoxid zum β-Hydroxynitril 3, dessen Tosylierung und schließlich Eliminierung von Toluol-sulfonsäure mit Kalium-tert-butoxid. – Mit Hilfe der Röntgenstrukturanalyse wurden für das Bicyclo[1.1.0]butan-Gerüst von 2b der Interplanarwinkel zu 111.8° und die Länge der Zentral-bindung zu 1.464 Å ermittelt. Additions of Benzvalene to Nitrile Oxides. A Synthesis for Benzvalene-3-carbonitrile 2,4,6-Trimethylbenzonitrile oxide, benzonitrile oxide, and fulminic acid undergo cycloaddition to benzvalene (1) to give the Δ2-isoxazolines 2a – c in high yields. By means of competition experiments the ratio of the rate constants for the reactions of 1 and norbornene with benzonitrile oxide has been determined to be kbenzvalene/knorbornene ≈ 1. The adduct 2c of fulminic acid was transformed to benzvalene-3-carbonitrile (4) by the following simple sequence: ring opening by sodium methoxide to yield the β-hydroxycarbonitrile 3, tosylation of 3, and, finally, elimination of toluenesulfonic acid with potassium tert-butoxide. – From the X-ray structure analysis of 2b the dihedral angle and the length of the central bond of the bicyclo[1.1.0]butane moiety have been determined to be 111.8° and 1.464 Å, respectively." @default.
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• W2023592837 date "1986-03-01" @default.
• W2023592837 modified "2023-10-18" @default.
• W2023592837 title "Additionen von Benzvalen an Nitriloxide. Eine Synthese für Benzvalen‐3‐carbonitril" @default.
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• W2023592837 doi "https://doi.org/10.1002/cber.19861190318" @default.
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