1957 年 77 巻 9 号 p. 1024-1026
By the Ullmann reaction of bromobenzonitrile and potassium phenoxide, 2-, 3-, and 4-cyanodiphenyl ethers were prepared and their cleavage reaction with metallic sodium in liquid ammonia was examined. In the case of 2-cyano (I) and 4-cyano (II) compounds, the main decomposition products were benzylamine and phenol, and a trace of dibenzylamine was obtained as a by-product. On the other hand, 3-cyano compound was found to form 3-amidinodiphenyl ether as the main product, with a trace of phenol. As a result, it was found that this reaction proceeded towards severance of ether-type oxygen constituting the diphenyl ether of identical type, shown by (I) and (II) in the case of 2- and 4-cyano compounds and that, at the same time, the cyano group was reduced to the benzylamine type. On the contrary, the ether-type oxygen linkage in 3-cyano compound was comparatively resistant to the severance compared to that in the 2- and 4-cyanocompounds.