35234-79-8Relevant academic research and scientific papers
PHOTOINDUCED REACTIONS OF 3β-ACETOXYCHOLESTA-5,7-DIENE, 3β-ACETOXYCHOLEST-5-ENE, TETRAPHENYLCYCLOPENTADIENE AND 1,1-DIPHENYLETHYLENE WITH OXYGEN IN THE PRESENCE OF PHENYLSELENYL BROMIDE
Haynes, Richard K.,Hilliker, Audrey E.
, p. 509 - 512 (1986)
Whereas PhSeBr under irradiation with O2 in CH2Cl2 at -78 deg C acts as a photoxygenation catalyst to convert 3β-acetoxycholesta-5,7-diene and tetraphenylcyclopentadiene into the corresponding endoperoxides, and 3β-acetoxycholest-5-ene into 3β-acetoxycholest-5-en-7-one and the corresponding alcohols, it reacts with 1,1-diphenylethylene to give mainly a bromohydrin; bromine radicals arising by photodissociation of the PhSeBr are implicated as the active intermediates.
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.
