6383-63-7Relevant academic research and scientific papers
Ninhydrin as a source of naphthoquinone acetals and benzocycloheptenetrione derivatives, and the trapping of an oxacarbene derived from a cyclopentanone
Leinweber, Dirk,Schnebel, Matthias,Wartchow, Rudolf,Wey, Hans G.,Butenschoen, Holger
, p. 2385 - 2390 (2002)
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-expanded regioisomers rac-13 and rac-14 was obtained. Irradiation in the presence of fumarodinitrile unexpectedly gave the spirocyclic compound rac-15, which was characterized by X-ray crystallography, rac-15 is the trapping product of oxacarbene 16, thus demonstrating a rare case of a ring expansion of a cyclopentanone to give a six-membered ring oxacarbene, here leading to an orthoester. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Engineering reactions in crystals: Gem-dialkoxy substitution enables the photodecarbonylation of crystalline 2-indanone
Ng, Danny,Yang, Zhe,Garcia-Garibay, Miguel A.
, p. 7063 - 7066 (2007/10/03)
The photochemical reactivity of three 1,1,3,3-tetrasubstituted 2-indanones was investigated in solution and in crystals. While solution irradiation of tetramethyl-2-indanone 2 leads to 1-isopropenyl-2-isopropyl benzene 5 in high yield, crystals of 2 were
