77336-60-8Relevant articles and documents
Lewis-Acid-Catalysed Reaction of Oxygen with 1,3-Diphenylisobenzofuran, Tetraphenylfuran and Tetraphenylcyclopentadiene
Haynes, Richard K.,Peters, Jennifer M.,Wilmot, Ian D.
, p. 2653 - 2661 (2007/10/02)
1,3-Diphenylisobenzofuran is converted into o-dibenzoylbenzene (40-70percent) by oxygen, either in dichlorometane at -78 deg C in the presence of 1-2 equiv. of a variety of Lewis acids, or on silica gel at 20 deg C, in the dark.Tetraphenylfuran is converted into (Z)-dibenzoylstilbene (55-65percent) under the former conditions in the presence of 0.05 equiv. of I2 or SnI4 under irradiation from a tungsten lamp.The conversions, which correspond to a mono-oxygenation process, do not involve as intermediates the furan endoperoxides, which were independently generated from the furans by use of singlet oxygen. 2,5-Dimethylfuran and p-menthofuran do not react with oxygen in the presence of Lewis acids under the foregoing conditions.Tetraphenylcyclopentadiene is converted by oxygen into the corrsponding endoperoxide (70-85percent) in the presence of 0.05 equiv. of I2 and SnI4 or 0.1 equiv. of Ph3C+BF4- in dichloromethane at -78 deg C under irradiation.
