Ninhydrin as a Source of Naphthoquinone Acetals and Benzocycloheptenetrione Derivatives, and the Trapping of an Oxacarbene Derived from a Cyclopentanone

D Leinweber, M Schnebel, R Wartchow…

Index: Leinweber, Dirk; Schnebel, Matthias; Wartchow, Rudolf; Wey, Hans G.; Butenschoen, Holger European Journal of Organic Chemistry, 2002 , # 14 p. 2385 - 2390

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Abstract

Abstract 1, 3-Bis (ethylenedioxy)-2-indanone (2) was shown to react with some dienophiles to give naphthoquinone acetals under photochemical reaction conditions, presumably by photodecarbonylation via the corresponding ortho-quinodimethane. With maleic anhydride the highly oxygenated benzocycloheptane derivative rac-12 was obtained in good yield. In a similar manner, upon irradiation in the presence of acrylonitrile a 2: 1 mixture of ring- ...