Hydroxylated Stearic Acids. II. The Periodate Oxidation of the 9,10-Dihydroxystearic Acids and the 1,9,10-Trihydroxyoctadecanes^1a

Abstract

The quantitative oxidative cleavage of vicinal hydroxyl groups by the. action of periodic acid to yield two carbonyl compounds was first demonstrated by Malaprade,lb and it was later postulated by Criegee2 and co-workers that the reaction proceeded through an acidic cyclic ester which decomposed with water to yield the observed products.

Stereochemical Studies in the Morphine Series. The Relative Configuration at Carbons Five and Six

“…Of the several methods available for determining the relative configuration of the hydroxyls in a cyclic 1,2-diol (5), the rate of oxidation by lead tetraacetate appeared to be the most suitable. Recent work, especially with cyclic sugar derivatives, has firmly established the original observation (14) that cis-1,2-diols are oxidized more rapidly than irons.…”

“…An examination of the curves also shows that the rate of oxidation of the one isomer was about three times as rapid as that of the other. 5 Since the compounds in which the aromatic nucleus has been opened already have the "morphi" designation, the morphine nomenclature has been retained throughout.…”

Thin-Layer Chromatographic Separation of Isomers of Ascorbic Acid and Dehydroascorbic Acid as Sodium Borate Complexes on Silica Gel and Cellulose Plates

“…Sodium borate or boric acid is known to form complexes with glycols, probably by chelation in many types of organic compounds. Complex formation is proposed to take place more readily with threo glycols than with erythro isomers (Wittcof et al, 1948;Frah and Mills, 1959;Loomis and Durst, 1992). Thin-layer plates containing complexing agents have been used for the separation of sugars (Pasturka, 1961) and hydroxy fatty acids (Morris, 1963;Roomi et al, 1966).…”

Long-chain unsaturated fatty acids as essential bacterial growth factors. Substances able to replace oleic acid for the growth of Corynebacterium ‘Q’ with a note on a possible method for their microbiological assay

“…had an I2 number of 102 (Trappe, 1938), and gave an acid with an equivalent of 256. The dihydroxystearic acids were prepared by the methods of Wittcoff, Moe & Iwen (1948) and Scanlan & Swern (1940). Elaidic acid was prepared by the method of Bertram (1936).…”