The disulfide functionality is present in a number of organic compounds of interest in the fields ofboth chemistry and biology. Because the disulfide group is known to be highly susceptible to furtheroxidation by a wide range of agents, performing a chemoselective oxidation without further oxidizingthe disulfide moiety poses a synthetic challenge. Reported herein are the first examples of such achemoselective oxidation in which a series of novel secondary alcohol disulfides 2a−f have beenconverted to the corresponding symmetrical diketones 3a−f utilizing a modified Swern oxidation.