Preparation and Characterization of Destructible Surfactants

Article abstract of DOI:10.1021/jo00341a026

Surfactants have been designed and prepared specifically for the application of surfactant-based media to organic synthesis.Condensation of 5-chloro-2-pentanone with 1,2-dodecanediol (3) yielded 2-methyl-2-(3-chloropropyl)-4-decyl-1,3-dioxolane (6), which on reaction with quinuclidine and pyridine gave 1-<3-(4-decyl-2-methyl-1,3-dioxolan-2-yl)propyl>-1-azoniabicyclo<2.2.2>octane chloride (1) and 1-<3-(4-decyl-2-methyl-1,3-dioxolan-2-yl)propyl>pyridinium chloride (2a), respectively.Ketal-based surfactants 1 and 2a are stable under neutral and basic conditions but readily hydrolyze under acidic conditions to 1-(4-oxopentyl)-1-azoniabicyclo<2.2.2>octane chloride (4) and 1-(4-oxopentyl)pyridinium chloride (5), respectively, and diol 3.In catalysis of the potassium permanganate oxidation of piperonal to piperonylic acid and the aqueous sodium hydroxide hydrolysis of α,α,α-trichlorotoluene to benzoic acid, surfactants 1 and 2a are about as effective as cetyltrimethylammonium bromide.