Synthesis and reactivity of ethoxyvinyl derivatives of 1,3-dioxolanium salts

2-(-Ethoxyvinyl)dioxolanium salts were obtained by reaction of ortho esters with 2,4,4,5,5-pentamethyl-1,3-dioxolanium perchlorate in acetic anhydride. Alkaline hydrolysis of 2-(-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate leads to the corresponding ,-unsaturated aldehyde. Substituted 2-(-aminovinyl)-1,3-dioxolanium perchlorates are formed by reaction of this salt with aromatic amines, amino acids, and urea. These perchlorates readily split out perchloric acid in alkaline media to give Schiff bases. The charges and electron densities were calculated for the 2-(-methoxyvinyl)-1,3-dioxolanium cation.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1614–1617, December, 1973.