Title: 1.3‐Dipolare Cycloadditionen, 68. Additionen der Nitriloxide an CN‐Mehrfachbindungen
Abstract: Aromatisch und aliphatisch substituierte Azomethine (Aldimine, Ketimine) treten mit Benzonitriloxid zu Δ2-1.2.4-Oxadiazolinen in guter Ausbeute zusammen (19 Beispiele). 2.4.6-Trimethyl-benzonitriloxid vereinigt sich mit Phenylisocyanat zum 1.2.4-Oxadiazolinon-(5) 25. Für die zu 1.2.4-Oxadiazolen führende Addition von Nitriloxiden an Nitrile (14 Beispiele) bewährt sich die in situ-Arbeitsweise; Nitrile sind schwächere Dipolarophile als Azomethine. Aromatische Nitrile sowie elektronenanziehend substituierte aliphatische Nitrile sind genügend aktiv. 1.3-Dipolar Cycloadditions, 68. Additions of Nitrile Oxides to CN-Multiple Bonds Azomethines with aromatic or aliphatic substituents (aldimines, ketimines) react with benzonitrile oxide to give Δ2-1.2.4-oxadiazolines in good yields (19 examples). 2.4.6-Trimethyl-benzonitrile oxide combines with phenyl isocyanate to give the 1.2.4-oxadiazolin-5-one 25. The cycloaddition of nitrile oxides to nitriles leads to 1.2.4-oxadiazoles (14 examples). Here the in situ technique in generation of the nitrile oxide is advantageous, because nitriles are dipolarophiles of lower activity than azomethines. Aromatic nitriles are sufficiently active as are aliphatic nitriles with electron-attracting substituents.
Publication Year: 1972
Publication Date: 1972-09-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 40
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