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The thermolysis of aryl desyl ethers. Formation of furan derivatives

Gaber A. E.-A. M.

Bulletin of the Polish Academy of Sciences. Chemistry

1998

Vol. 46, No. 2

185-193

Thermal reactions of aryl desyl ethers PhCOCH(OAr)Ph (Ar = Ph, p-tolyl) 1, 2 gave 2,3-diphenylbenzo(b)furan 5a,b and phenols as major products in addition to small amounts of toluene, benzil, benzoic acid, benzophenone, arylbenzoate, p-benzylphenol, 2,3,4,5-tetraphenylfuran 4 and 2,3-diphenylbenzo (l,4) dioxin 6a,b. In the presence of isoquinoline as a radical trap, 1 gave 1-phenylisoquinoline beside the previous products. Analogous results, in addition to diphenylmethane and benzophenone as major products as well as 1,1,2,2-tetraphenyl ethane and dibenzhydryl ether as minor products, were also obtained on heating the benzhydryl desyl ether 3. A free radical mechanism has been postulated to take place through the initial homolysis of the C-OAr bond to account for the identified products.