Heteroaromatic azo compounds as efficient and recyclable reagents for direct conversion of aliphatic alcohols into symmetrical disulfides

4,4′-Azopyridine 1a and 5,5′-dimethyl-3,3′-azoisooxazole 1e are used for the efficient, direct, and selective conversion of aliphatic alcohols into their corresponding disulfides in high yields under Mitsunobu conditions in combination with PPh3 and NH4SCN. The reaction with 1a occurs homogeneously, and 1e heterogeneously. In both reactions, the produced N-cyanohydrazines are isolated and reoxidized to the corresponding azo compounds easily.