Diphenylketene-p-Tolylimine

Stevens and French synthesized diphenylketene-p-tolylimine (4) by dechlorination of the precursor (3) by refluxing it with one equivalent amount of sodium iodide in acetone for 90 min. The product (4) is a bright yellow solid which reacts with water, ethanol, and chlorine in the same way that ketenes react. 

Oxidation of hydroxy steroids. Hydroxy steroids are oxidized to keto steroids in about 60% yield by the combination of N,N-diethyl-l-propynylamine-DMSO catalyzed by phosphoric acid. Benzene is used as solvent.1 In later work2 the combination of diphenylketene-p-tolylimine and DMSO was used with somewhat improved yields (compare Pfitzner-Moffatt reagent). 

Various alternative systems for oxidizing steroidal alcohols have been reported, where diphenylketen-p-tolylimine, AW-diethylaminopropl-yne, or W-dimethylaminophenylacetylene are added to mixtures of DMSO and acid. ... 

A soln. of diphenylketene p-tolylimine and azobenzene in anhydrous ether refluxed at least 4 days under a sun lamp l,2,4,4-tetraphenyl-3-p-tolylimino-1,2-diazetidine. Y 83%. F. e. s. M. W. Barker and M. E. Goker, J. Heterocyclic Ghem. 4, 155 (1967). 

Severals drops of coned. HGl added to a soln. of diphenylketene-N-p-tolylimine in commercial undried dimethyl sulfoxide, swirled, and the product isolated... 

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