Benzil oxime from

Using a quadridentate ligand derived from 1,3-propanediamine and 2,3-butanedione the cobalt-oxime complex (61) was prepared, and again in presence of the chiral base quinine (60) this was used to hydrogenate benzil according to equation (54) in an optical yield of 79%.277 These cobalt systems permitted only low turnover numbers to be achieved. 

Benzil acts like a ketone in that it forms oximes with hydroxylamine-The oximes are of exceptional interest, since our knowledge of the stereochemistry of nitrogen proceeds from them. Benzil forms two monoximes and three dioximes. The constitution of these compounds will be discussed later, under the preparation of benzophenone-oxime ... 

The third reaction type to be discussed in this section is the Forster reaction. It was discovered by Forster in 1915, as he had obtained (benzoyl)(phenyl)diazomethane (2-diazo-l,2-diphenylethan-l-one, 2.62) by treatment of (Z)- and ( )-benzil monooxime ((Z) = 2.95) with sodium hypochlorite and ammonia (which readily forms chloramine). a-Keto-monoximes like 2.95 are obtained easily from a-methylene-con-taining ketones (e.g., 2.94) by the oximation reaction, i.e., a nitrosation with a nitrous acid ester followed by a C O proton shift (2-41). 

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