α,β-Unsaturated esters from the tri-n-butylarsine-promoted reaction of bromomalonic esters with aldehydes

Article abstract of DOI:10.1016/0022-328X(89)85082-X

A convenient synthesis of α,β-unsaturated esters (in 68-96percent yields) from the reaction of a bromomalonic ester with aldehydes promoted by tri-n-butylarsine is descriebed.A mechanism involving halophilic attack of tri-n-butylarsine leading to the formation of a salt followed by reaction with carbonyl compounds is proposed.This methodology provides a convenient route to α,β-unsaturated esters and represents an alternative to the Knoevenagel reaction.