Uses
Diphenylketene is used for acylation of carboxylic acids to give mixed anhydrides; cycloaddition with a variety of unsaturated
compounds; synthetic source of diphenylallenes.
Preparation
Preparative Methods of Diphenylketene: originally prepared by zinc reduction of α-chlorodiphenylacetyl chloride; oxidation
of benzil monohydrazone with yellow Mercury(II) Oxide followed by thermal rearrangement of the α-diazo
ketone; dehydrohalogenation of diphenylacetyl chloride with Triethylamine; debromination of α-
bromodiphenylacetyl bromide by the action of Triphenylphosphine.
Synthesis Reference(s)
Journal of the American Chemical Society, 93, p. 4604, 1971
DOI: 10.1021/ja00747a050Organic Syntheses, Coll. Vol. 3, p. 356, 1955
storage
Diphenylketene stored in a tightly stoppered bottle at 0 °C is stable for several
weeks. Trace amounts of hydroquinone and storage under nitrogen inhibit polymerization and lead to
increased stability. Given the reactivity of diphenylketene with amino acids, care should be taken to avoid
skin contact.
