Abstract:Structure of "7-Dehydrocholestene Isomer" 107 with 75 ml. of water and heated to 90°. The solution was chilled and the solid recrystallized from water. The yield of a-chloro-a-£-tolylsulfonylacetamide (I) was 1 g. (4.4%), m. p. 162-165°. Repeated recrystallizations from water and alcohol gave «-^-tolylsulfonylacetamide.Reaction of Sodium «-Butyl Mercaptide with Dichloroacetamide.-To 10.7 ml. (9 g., 0.10 mole) of «-butyl mercaptan was added a sodium ethoxide solution prepared by dissolving 2.3 g. (0.10 gram ato… Show more
“…21 Final proof of the location of the new oxy- Vol. 29 Chart I from its ready acetylation with acetic anhydride in pyridine, while the 9a configuration is based on the usual over-all cis addition of water by the hydration reaction. (See Chart I.)…”
The diol LV (0.5 g. in 40 cc. of tetrahydrofuran) was hydrated by method a, and the product was chromatographed on 15 g. of alumina. Elution with chloroform-methanol (4:1)
“…21 Final proof of the location of the new oxy- Vol. 29 Chart I from its ready acetylation with acetic anhydride in pyridine, while the 9a configuration is based on the usual over-all cis addition of water by the hydration reaction. (See Chart I.)…”
The diol LV (0.5 g. in 40 cc. of tetrahydrofuran) was hydrated by method a, and the product was chromatographed on 15 g. of alumina. Elution with chloroform-methanol (4:1)
The oxygen atom of the carbonyl group in aldehdyes and ketones can be replaced by hydrogen by heating the semicarbazone, the hydrazone, or the azine in the presence of an alkaline catalyst. This reaction is known as the Wolff‐Kishner reduction. Two slightly different variations of the method were discovered independently by Kishner in 1911 and by Wolff in 1912. Though the Kishner method has the advantage of avoiding the necessity of a sealed tube, the Wolff method has been modified to obviate both this necessity and that of isolating the intermediate carbonyl derivative. This reduction is the subject of this chapter.
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