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- W2037478419 abstract "Cycloaddition of bifunctional nitrones 1 containing a nitrone function as part of the 1,4-diazabutadiene system to electron-rich monosubstituted alkenes has been investigated. The nitrone group manifested predominant 1,3-dipolar reactivity compared with that of the 1,3-heterodiene system leading to isoxazolidine derivatives 2 and 3. An atypical assistance of the 1,4-diazabutadiene system was demonstrated by a reverse regioselectivity of cycloadditions to allyl alcohol yielding bicyclic heterocycles 2 via 3,4-disubstituted isoxazolidines. Cycloadditions with allyl halides gave 3,5-disubstituted isoxazolidines 3 showing common regioselectivity for the nitrone function. The mechanism and configuration of the products are discussed. Cycloaddition von bifunktionellen Nitronen an monosubstituierte Alkene, I Die Cycloaddition der bifunktionellen Nitrone 1, die die Nitronfunktion als Teil eines 1,4-Diazabutadien-Systems enthalten, an elektronenreiche monosubstituierte Alkene wurde untersucht. Gegenüber dem 1,3-Heterodiensystem wies die Nitrongruppe eine bevorzugte 1,3-dipolare Reaktivität auf, wobei die Isoxazolidinderivate 2 und 3 entstanden. Eine atypische Beteiligung des 1,4-Diazabutadiensystems zeigte sich durch eine umgekehrte Regioselektivität der Cycloadditionen an Allylalkohol, die bicyclische Heterocyclen 2 über 3,4-disubstituierte Isoxazolidine ergaben. Cycloadditionen mit Allylhalogeniden führten gemäß der üblichen Regioselektivität der Nitrofunktion zu 3,5-disubstituierten Isoxazolidinen 3. Der Mechanismus sowie die Konfiguration der Produkte werden diskutiert." @default.
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- W2037478419 date "1985-10-01" @default.
- W2037478419 modified "2023-09-23" @default.
- W2037478419 title "Cycloaddition of Bifunctional Nitrones to Monosubstituted Alkenes, I" @default.
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- W2037478419 doi "https://doi.org/10.1002/cber.19851181014" @default.
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