Cyano Phosphate: An Efficient Intermediate for the Chemoselective Conversion of Carbonyl Compounds to Nitriles

Article abstract of DOI:10.1021/jo00005a031

Cyanohydrin diethyl phosphates, readily obtained from various ketones and aldehydes by reaction with diethyl phosphorocyanidate and lithium cyanide, reacted chemoselectively with samarium(II) iodide in THF to give the corresponding nitriles in excellent yields.This method was also found applicable to α,β-unsaturated carbonyl compounds via cyano phosphates to give β,γ-unsaturated nitriles, not obtainable by standard methods, without isomerization of the double bonds.