Catalytic oxidation of alcohols to esters with Ru3(CO)12
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Alcohol Oxidation
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Alcohol Oxidation
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Abstract A tandem IBX‐promoted oxidation of primary alcohol to aldehyde and opening of intermediate β,γ‐diolcarbonate aldehyde to ( E )‐γ‐hydroxy‐α,β‐enal has been developed. Remarkably, the carbonate opening delivered exclusively ( E )‐olefin and no over‐oxidation of γ‐hydroxy was observed. The method developed has been extended to complete the stereoselective total synthesis of both ( S )‐ and ( R )‐coriolides and d ‐ xylo ‐ and d ‐ arabino ‐C‐20 guggultetrols.
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The oxidation with t-butyl chromate has been carried out with benzyl alcohol, its p-substituted derivatives and trans-cinnamyl alcohol, and also with β-phenylethyl alcohol. In the former alcohols, the corresponding aldehyde was obtained as the main product, but the corresponding ester was not formed. On the other hand, the latter alcohol, containing a methylene group adjacent to the hydroxymethyl group, produced the corresponding ester, aldehyde and acid, as in the case of a saturated primary aliphatic alcohol.
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Abstract Increased versatility has been achieved in the identification of unknown olefinic fatty acids by ozonolysis. The method has been applied to purified methyl esters containing up to four double bonds. Aldehydic fragments, obtained from esters by the Stein‐Nicolaides procedure (2), were determined by GLC on two columns of different polarity. Equivalent chain lengths of each fragment on the two columns provide identification. For monoenoic esters the location of the double bond is clearly indicated by the aldehyde and aldehyde‐ester fragments. Dienes are identified by the aldehyde and aldehyde‐ester fragments when the original chain length of the ester is known; the dialdehyde fragment provides confirmatory evidence. Trienes and tetraenes are analyzed by interrupting the ozonolysis at various times, thereby producing unsaturated, as well as saturated, aldehydes and aldehyde‐esters. Unsaturated fragments locate the central or interior double bonds.
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The development of 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO; 1,5-dimethyl-Nor-AZADO, 2) as an efficient catalyst for the selective oxidation of primary alcohols in the presence of secondary alcohols is described. The compact and rigid structure of the azanoradamantane nucleus confers potent catalytic ability to DMN-AZADO (2). A variety of hindered primary alcohols such as neopentyl primary alcohols were efficiently oxidized by DMN-AZADO (2) to the corresponding aldehydes, whereas secondary alcohols remained intact. DMN-AZADO (2) also has high catalytic efficiency for one-pot oxidation from primary alcohols to the corresponding carboxylic acids in the presence of secondary alcohols and for oxidative lactonization from diols.
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The oxidation of alcohols by argentic picolinate has been studied and has been shown to give high yields of aldehyde and ketone. Examination of the oxidation of aldehydes shows that smooth conversion to the acid occurs in most cases, but in some cases, an anomalous reaction occurs, which probably involves attack upon the aromatic ring of substituted benzaldehydes. The oxidation of aldehydes occurs much more slowly than alcohol-oxidation under similar conditions.
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