A 13C‐NMR study of squalene some aspects of the selective terminal oxidation of squalene

Abstract

Abstract13CNMR data (shifts and relaxation times) show that the conformational equilibrium and the intramolecular mobility of squalene are very similar in media of different polarity. This is inconsistent with one of van Tamelen's original proposals explaining the selective terminal epoxidation in terms of tight coiling of squalene in polar media. MINDO/2′ calculations predict that terminal epoxidation is favoured over internal epoxidation by ∼1.5 kcal/mole.