The Reaction of Propiolic Acid Esters with Tertiary Amines. Formation of Betaines

Abstract

Reaction of propiolate esters, H—C≡C—CO 2 R, with tertiary alkylamines R′ 3 N in highly aqueous media yields betaines of the type trans R′ 3 N + •CH=CH•CO 2 − . The spectral and chemical properties of these derivatives are discussed as well as the mechanism of their formation. The major by-product of reaction is the corresponding trans-3-alkoxyacrylate RO—CH=CH—CO 2 R.