Albright and Goldman

Following closely on the foregoing oxidation procedure, Albright and Goldman (1,2) described a novel method for the oxidation of alcohols which uses methyl sulfoxide and certain acid anhydrides—e.g., acetic... 

The use of trifluoroacetic anhydride for the activation of DMSO in the oxidation of alcohols was first attempted by Albright and Goldman in 196 5.119,120 According to these authors, who tried the reaction at room temperature, trifluoroacetic anhydride is not effective in the activation of DMSO. Later, Swern et al. made a detailed study of the interaction of DMSO with TFAA,121 and proved that the resulting activated DMSO is stable at low temperature and can be used in the oxidation of alcohols. In... 

Dyer et al. oxidized a furanoside derivative by the DMSO-DCC-pyridinium phosphate method, and Albright and Goldman applied the Pfitzner-Moffatt procedure successfully for oxidation of yohimbine and other indole alkaloids. Suscep-... 

C.iii. Other DMSO Oxidations. Albright and Goldman developed a reagent using DMSO and acetic anhydride that formed an active sulfoxonium complex. 12 jj (jje initial work, yohimbine was oxidized to the ketone (yohimbinone) in 85% yield, at ambient temperatures in 24 h. 2 As with DCC, DMSO initially reacts with acetic anhydride to form sulfoxonium salt 66, which then reacts with the alcohol. Acetate is the leaving... 

This reaction was first reported by Albright and Goldman from the American Cyanamid Company in 1965. It is a mild conversion of primary and secondary alcohols into corresponding aldehydes and ketones using the mixture of dimethyl sulfoxide and acetic anhydride as the oxidant. This reaction is particularly useful for the oxidation of the steri-cally hindered hydroxyl groups. In general, the oxidation is carried out by allowing a mixture of 1 mmol primary or secondary alcohol, 3 mL DMSO, and 2 mL (20 mmol excess) acetic anhydride to stand at room temperature for 18-24 h. ... 

A mixture of yohimbine, dimethyl sulfoxide, and acetic anhydride allowed to stand 18-24 hrs. at room temp. yohimbinone. Y 80-85%. — This method is particularly useful for the oxidation of sterically hindered hydroxyl groups and compounds, such as indole alkaloids, which are sensitive to non-selective oxidants. F. e. s. J. D. Albright and L. Goldman, Am. Soc. 87, 4214 (1965) carbohydrates s. 289. 

Triflouroacetic anhydride was used before oxalyl chloride and is also known as the Swern Oxidation. Acetic anhydride can also be used. (Albright-Goldman Oxidation)... 

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