Effect of Inverse Micelles on the Competition between Lactonization and Polymerization Reactions of an ω-Hydroxy Carboxylic Acid

Article abstract of DOI:10.1021/jo00337a028

The ability of inverse micelles to influence the competition between carbodiimide-mediated lactonization and polymerization of 15-hydroxypentadecanoic acid (1), yielding pentadecanolide (2) and polymer (3), respectively, has been investigated by using inverse micellar systems in benzene based on di-n-dodecyldimethylammonium bromide (DDABr) and on bis(2-ethylhexyl) sodium sulfosuccinate (AOT) with and without water pools.Two ionic carbodiimides, 1-cyclohexyl-3-<2-(N-methylmorpholinio)ethyl>carbodiimide p-toluenesulfonate (4) and 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (5), were used.The inherent ability of carbodiimide 4 to effect lactonization of 1 is inhibited moderately by DDABr inverse micelles without water pools and completely by AOT inverse micelles without water pools.Carbodiimide 4 did not effect esterification when these inverse micellar systems contained water pools; carbodiimide 5 apparently did not do so under any of the conditions used.