A. Oku, K. Shimada, F. Mashio
1973
Citations
0
Influential Citations
5
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The oxidation of tetraphenylallene (1) with m-chloroperbenzoic acid has been reported. Under acidic conditions, 1-hydroxy-1,3,3-triphenyl-2-indanone (2) was isolated in 45% yield, along with benzophenone (3) and the m-chlorobenzoate of 2 as minor products. In the presence of sodium carbonate, the oxidation products were 2,2,4,4-tetraphenyloxetanone (6), 3, and 1,3,3-triphenyl-2,3-dihydro-5H-indene-2,5-dione (5). The prolonged oxidation of 2 with per ace tic acid yielded α,α-diphenylphthalide (9a). The alkaline hydrolysis of 2 induced ring cleavage to give o-benzhydrylbenzilic acid (15b), whereas acid hydrolysis in ethanol or methanol gave the corresponding ethers, 16a and 16b respectively.