Acid-catalysed transformation of oleic acid, and 12-hydroxystearic acid, into γ-octadecanolactone. Evidence for the occurrence of a novel side reaction

A Granata, F Sauriol, AS Perlin

文献索引：Granata, Alessandro; Sauriol, Francoise; Perlin, Arthur S. Canadian Journal of Chemistry, 1994 , vol. 72, # 7 p. 1684 - 1690

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被引用次数: 5

摘要

γ-Octadecanolactone is produced in the reaction between oleic acid (cis-9-octadecenoic acid) and concentrated sulfuric acid at 80° C. To account for its formation, two types of mechanism have been considered. Both begin with protonation at C-9/C-10 to give a carbocation, following which the positive charge is transmitted to C-4, where nucleophilic attack by the carboxyl group is facilitated. One of them invokes a" zipperlike" succession of ...