Singlet oxygen formylation

Indoles were high (0.02-1.2), evidence that auto-catalysls occurred In distilled water. In aqueous CRM-1, Indoles underwent sensitized photolysis, possibly through a superoxide or singlet-oxygen Intermediate. The same photoproduct of 3-MI, o-(N-formyl)amlnoacetophenone, was found In both distilled water and In aqueous CRH-1. Carbazole underwent direct photolysis In both distilled water and aqueous CRM-1, Indicating that It has a different photolysis mechanism from that of Indoles In the two systems studied. 

Electrochemical oxidation of tropanes" in acetonitrile involves the formation of methylene-NN-bis-nortropanyl, of N/V-bis-nortropanyl, of N-formyl-nortropine, and of N-cyanomethyl-nortropane. Dye-sensitized singlet oxygen, produced by laser excitation," converts tropinone into iV-formyl-nortropanone in moderate yields. Photochemical demethylation of cocaine to norcocaine has been carried out," but the yields are less satisfactory than in the chemical ... 

The same 6-formyl-7-hydroxy-8-methoxycoumarin was later characterized as a direct photolysis product of 8-MOP with the involvement of singlet oxygen, generated by the psoralen. ... 

Spectrographic characterization. The infrared spectrum of the mixed anhydride shows bands in the carbonyl region at 1765 and 1791 cm-1 and carbon-oxygen-carbon stretching absorption at 1050 cm 1 (a band at 1180 cm-1 could also be due to C—O—C). The NMR spectrum shows singlets at S = 2.25 (acetyl protons), and at S = 9.05 (formyl proton). 

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