Mechanistic studies regarding the oxidation of alcohols by silver carbonate on celite

Abstract

The mechanism of the oxidation of alcohols by silver carbonate on Celite was thoroughly investigated to ascertain the nature of the transition state and the possible intervention of reaction intermediates. Kinetic, stereochemical, and isotopic labeling techniques were used to differentiate among the various theoretically plausible mechanistic alternatives. The effects of surface adsorption and solvent composition on the outcome of the reaction were also studied. The data were consistent with a concerted process for which a model is proposed.

Optical absorption of polyethylene glycol (PEG) modified silica matrix embedded with nanocrystalline silver

“…This strongly supports the idea that addition of PEG in the matrix helped reduction of Ag ion to Ag metal at a relatively low temperature. Alcohols are well-known reducing agents and their role in reducing silver ions to metals was also confirmed by Kakis et al [15]. Polyethylene glycol, with its hydroxyl end members, is likely take part in similar reducing reaction:…”

Modular Synthesis and Biological Investigation of 5-Hydroxymethyl Dibenzyl Butyrolactones and Related Lignans

“…Transformation of C-5 hydroxymethyl analogues 4 into dibenzylbutryolactone lignans 1 was achieved via reduction using LiAlH 4 , to the corresponding triols 38aa – bd , followed by periodate cleavage, forming lactols 39aa – bd . These lactols 39aa – bd were then oxidised using Fetizon’s reagent [37,38] to give racemic samples of dibenzyl butyrolactone lignans 1aa – bd , including known natural products arcitin 1aa , bursehernin 1ab , (3 R* ,4 R* )-3-(3″,4″-dimethoxybenzyl)-4-(3′,4′,5′-trimethoxybenzyl)dihydrofuran-2(3 H )-one 1ac , kusunokinin 1ba , hinokinin 1bb, and isoyatein 1bc . Additionally, phenolic lignans, buplerol 1ae , and haplomyrfolin 1be were produced by the debenzylation of 1ad and 1bd , respectively.…”

Accessing Single Enantiomer Strigolactones: Progress and Opportunities

“…Alkylation with iodoacetonitrile gave the stereochemically undefined nitrile 72 . Global reduction of the enone, ester, and nitrile with DIBAL, afforded a lactol intermediate, which was oxidized using Fétizon's reagent to give 73 in low overall yield.…”