Topic
Oxidation of secondary alcohols to ketones
About: Oxidation of secondary alcohols to ketones is a research topic. Over the lifetime, 61 publications have been published within this topic receiving 1887 citations.
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TL;DR: In this article, an effective synthesis of carbamoyl azides directly from primary alcohols using iodobenzene dichloride in combination with sodium azide has been developed.
Abstract: An effective synthesis of carbamoyl azides directly from primary alcohols using iodobenzene dichloride in combination with sodium azide has been developed. Moreover, the same regent combination was also efficient for the oxidation of secondary alcohols to the corresponding ketones.
15 Apr 2001
TL;DR: InChIKey as mentioned in this paper ] is a key for storing ammonium heptamolybdate tetrahydrate tetrahedrate under air, which can be used and stored at rt under air.
Abstract: (H2O2) [7722-84-1] H2O2 (MW 34.02)
InChI = 1S/H2O2/c1-2/h1-2H
InChIKey = MHAJPDPJQMAIIY-UHFFFAOYSA-N
((NH4)6Mo7O24) [12027-67-7] H24Mo7N6O24 (MW 1163.88)
((NH4)6Mo7O24·4H2O) [12054-85-2] H32Mo7N6O28 (MW 1235.96)
(epoxidation;2 oxidation of secondary alcohols to ketones;2, 3 oxidation of aldehydes to acids;2 chemoselection between epoxidation and alcohol oxidation2, 4)
Physical Data: (NH4)6Mo7O24·4H2O: dec 190 °C; d 2.498 g cm−3.
Solubility: (NH4)6Mo7O24·4H2O: sol H2O (43 g/100 mL); insol alcohol.
Form Supplied in: (NH4)6Mo7O24·4H2O: colorless or slightly greenish or yellowish crystals; widely available.
Handling, Storage, and Precautions: (NH4)6Mo7O24·4H2O: commercially available ammonium heptamolybdate tetrahydrate can be used and stored at rt under air. For H2O2, see Hydrogen Peroxide.
TL;DR: In this article, hydrogen peroxide in conjunction with ammonium molybdate effects the epoxidation of olefins, the oxidation of secondary alcohols to ketones, and the oxidization of aldehydes to acids.
Abstract: Hydrogen peroxide in conjunction with ammonium molybdate effects the epoxidation of olefins, the oxidation of secondary alcohols to ketones, and the oxidation of aldehydes to acids. By controlling pH olefin epoxidation can be suppressed in favor of alcohol oxidation. Secondary alcohols are cleanly oxidized in the presence of primary alcohols. Sterically more hindered alcohols are oxidized more rapidly than less hindered alcohols. The latter rate preference permitted selective conversion of a 17-hydroxyl group of several steroids into a.ketone in the presence of a 3-hydroxyl group. The chemoselective oxidation of aldehydes to carboxylic acids is another use of this inexpensive oxidation system. A rate acceleration by addition of the lanthanide salt cerium chloride is noted and attributed to enhanced rates of hydration of the aldehyde. Potential mechanisms are discussed.
TL;DR: Secondary alcohols are rapidly oxidized to ketones by a solution of trichloroisocyanuric acid in acetone as discussed by the authors, which is known as TOCA.
Abstract: Secondary alcohols are rapidly oxidized to ketones by a solution of trichloroisocyanuric acid in acetone.