Preparation of ketones from nitriles and phosphoranes

ORGN 615

D. F. Taber and Lisi Cai. Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716
The ketone is the central functional group in organic synthesis. One route to a ketone is the addition of an organometallic reagent to the nitrile. The disadvantage of this approach is that any unreacted organometallic reagent is protonated on work-up and so lost. We report an improvement of the McEwen procedure, addition of a phosphorane to the nitrile. The advantage of this approach is that any unreacted phosphonium salt can easily be recovered and reused.