Tetrahedron Letters p. 509 - 512 (1986)
Update date:2022-08-04
Topics: Experimental conditions Oxygen 1,1-diphenylethylene Photoinduced reactions 3β-acetoxcholesta-5,7-diene 3β-acetoxcholest-5-ene Tetraphenylcyclopentadiene Phenylselenyl bromide
Haynes, Richard K.
Hilliker, Audrey E.
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.
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