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- W2068656994 abstract "Abstract A mechanistic study, principally based on product analysis, relative to the TiO 2 ‐photosensitized oxidation of indane and some of its hetero‐analogues, in deaerated CH 3 CN and in the presence of Ag 2 SO 4 , was performed. In particular: (i) 1‐acetamidoindan (principal product), indene, 1‐indanol and 1‐indanone were obtained from indan; (ii) 5‐methoxyindan gave 6‐methoxyindene (principal product) and 5‐methoxy‐1‐indanone; (iii) 2,3‐dihydrobenzofuran, 2,3‐dihydroindole and 2,3‐dihydrobenzothiophene produced benzofuran, indole and benzothiophen (the last one accompanied by minor amounts of 2,3‐dihydrobenzothiophene‐1‐oxide), respectively. Considering the previous studies on photo‐oxidation of analogous substrates as benzylic derivatives (arenes, alcohols and ethers) and from reaction product profiles, an electron‐transfer mechanism (from the substrate to the photogenerated hole) is suggested, where the radical cation intermediate should deprotonate to a benzylic radical. The carbocation obtained from the oxidation of this radical should competitively evolve to alkene, alcohol and acetamide. H 2 18 O labelling photo‐oxidation experiments suggest that the ketone, when present, should derive from the substrate, through the alcohol as intermediate. Copyright © 2006 John Wiley & Sons, Ltd." @default.
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- W2068656994 date "2006-06-01" @default.
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- W2068656994 title "TiO2-sensitised photo-oxidation mechanism of indane and some of its hetero-analogues in deaerated CH3CN" @default.
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- W2068656994 doi "https://doi.org/10.1002/poc.1086" @default.
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