Abstract
Thermal reactions of aryl desyl ethers PhCOCH(OAr)Ph (Ar=Ph, p-tolyl) I and II gave 2,3-diphenylbenzo[b]furan 1a,b and phenols 2 and 3 as major products, in addition to small amounts of toluene 4, benzil 5, benzoic acid 6, benzophenone 7, aryl benzoate 8 and 9, p-benzylphenol 10, 2,3,4,5-tetraphenylfuran 11 and 2,3-diphenylbenzo[1,4]dioxin 12a,b. In the presence of isoquinoline as a radical trap, I gave 1-phenylisoquinoline 13 as well as the previous products. Analogously, in addition to diphenylmethane 14 and benzophenone 7 as major products, 1,1,2,2-tetraphenylethane 15 and dibenzhydryl ether 16 as minor products were obtained on heating the benzhydryl desyl ether III. 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.
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