Primary alcohols copper chloride

Acyl chlorides can he reduced to primary alcohols by reduction in aprotic solvents such as PEG, or using NaBHa-Alumina in Et20. More s)mthetically useful is the partial reduction to the aldehydic stage, which can be achieved by using a stoichiometric amount of the reagent at —70 °C in DMF-THF, with the system NaBHa-CadntiHwt Chloride-DMF, or with Bis(triphenylphosphine)copper(I) Borohydride. 

Reactions.—New systems for the reduction of alkyl halides to alkanes include mixtures of lithium aluminium hydride with transition-metal chlorides (such as Ni or Co" chlorides) and some complex metal hydrides of copper, especially the THF-soluble Li4CuHs. Details of the application of sodium cyanoborohydride to the reduction of halides (and sulphonate esters) in dipolar aprotic solvents have been published. Virtually all other functional groups are inert to this convenient, mild, and efficient system, which has been used to develop a one-pot deoxygenation of primary alcohols (Scheme 39) via the iodides. The alternative cyanoborohydride reagents (55) and the polymeric (56) are also discussed. ... 

Oxidations. Various primary and secondary alcohols are oxidized to give aldehydes and ketones by PdfOAcl -O -pyridine in the presence of 3A molecular sieves. Modified Wacker processes which obviate copper and chloride employ the Pd(OAcl -02 system and a water-soluble 1, 10-phenanthroline ligand or polypyrrole as redox-active ligand.- ... 

A condition known as absinthism was observed in chronic consumers of the alcoholic beverage absinthe, which contains wormwood extract. The condition was described as a form of alcoholism that included delirium, hallucinations, tremors, and seizures (Lee and Balick 2005). While the compound thujone was once thought to be the primary cause of the psychotropic activity and toxicity of absinthe, recent analyses of absinthe indicate that the thujone content of historical and contemporary samples is insignificant and that other ingredients, such as the coloring agents copper sulfate or antimony chloride, may have been responsible for the adverse effects of absinthe (Blaschek et al. 2002 Lachenmeier et al. 2008). 

Deamination via sulphonamide intermediates allows the conversion of the carbon-nitrogen bond into the carbon-oxygen bond. Conditions have been established such that nitrates may be obtained from the deamination of primary amines with dinitrogen tetroxide at low temperature rather than alcohols/ The oxidation of amines to nitriles has been carried out using copper(l) chloride in pyridine under an oxygen atmosphere/ which is a milder reagent than those previously used to perform this transformation. Cleavage of tertiary amines with ethyl chloroformate affords a simple preparation of di- and tri-substituted olefinic synthons (Scheme... 

Several references have appeared on the use of solid-phase oxidants. Solid potassium permanganate-copper sulphate mixtures oxidize secondary alcohols to ketones in high yield, and pyridinium chromate or chromic acid on silica gel are described as convenient off-the-shelf reagents for oxidation of both primary and secondary alcohols. Anhydrous chromium trioxide-celite effects similar transformations only when ether is present as co-solvent. An excellent review, with over 400 references, on supported oxidants covers the use of silver carbonate-celite, chromium trioxide-pyridine-celite, ozone-silica, chromyl chloride-silica, chromium trioxide-graphite, manganese dioxide-carbon, and potassium permanganate-molecular sieve. 

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