Thermochemical properties of dibenzyloxy disulfides

The in situ thermal behavior of dialkoxy disulfides (single bondOSSOsingle bond) has been previously explored, however their neat thermal stability has yet to be examined. We synthesized a library of ten dibenzyloxy disulfide derivatives with various para-substituents. Each derivative was analyzed by TGA and DSC to discern molecular fragmentation. A correlation of the pattern of fragmentation to Swain and Luptonʹs R-value was observed. Also, DSC analysis revealed that when the para-substituent was a phenyl (i.e. bis(p-phenylbenzyloxy) disulfide), and successive runs were performed, the thermogram showed the presence of the fragmentation, and upon 1H NMR analysis its corresponding alcohol and aldehyde were observed.