Summary
Arylnitrile oxides undergo regio- and stereo-specific 1,3-dipolar cycloaddition reactions with 5-acetoxy-2(5H)-furanone. In each case a single product3a–3g results from ananti approach to the 5-acetoxy substituent, the oxygen of the 1,3-dipole being attached to C-4 of furan. Under similar conditions 5-benzoyloxy-2(5H)-furanone yields3h–3i. The structures of the adducts were determined by1H- and13C-NMR spectroscopy.
Zusammenfassung
Arylnitriloxide reagieren mit 5-Acetoxy-2(5H)-furanon in einer regio- und stereoselektiven 1,3-dipolaren Cycloaddition. In jedem der untersuchten Fälle ergaben sich die einheitlichen Produkte3a–3g als Folge eineranti-Annäherung an den 5-Acetoxysubstituenten, wobei der Sauerstoff des 1,3-Dipols an das C-4 des Furans addiert. Unter ähnlichen Bedingungen ergab 5-Benzoyloxy-2(5H)-furanon die Produkte3h–3i. Die Strukturen der Addukte wurden mittels1H-und13C-NMR bestimmt.
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Oravec, P., Fišera, Ľ. & Gažo, R. Regio- and stereoselective 1,3-dipolar cycloaddition of arylnitrile oxides to 5-acetoxy-2(5H)-furanone. Monatsh Chem 122, 165–170 (1991). https://doi.org/10.1007/BF00809361
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DOI: https://doi.org/10.1007/BF00809361