Add time:09/24/2019         Source:sciencedirect.com

DCA-sensitized electron-transfer photooxygenation of TETRAPHENYLALLENE (cas 1674-18-6) (1) in acetonitrile yields benzophenone (3) and polymeric material. In acetone, the yield of 3 is better than twice the amount obtained in acetonitrile and very little of polymeric material is observed. If the acetone solution is worked-up immediately after the oxygen consumption ceased, 1,3-dihydroperoxy-1,1,3,3-tetrapheny]-2-propanone (8) is isolated. Its formation is proposed to occur via the peroxyallyl zwitterion 4 and the tetraphenylcyclopropanone (7) (Scheme 1). 8 decomposes slowly into 3, and CO + CO2 (3:1) in neutral solution; in the presence of a base, decomposition is fast, resulting in the formation of two molecules of 3, one molecule of water, and one molecule of CO2 . Decomposition of 8 in the presence of various fluorescers and a base yields a bright fluorescence of the additives.

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