Ditocopheryl Sulfides and Disulfides: Synthesis and Antioxidant Profile

Symmetrical ditocopheryl disulfides (Toc)(2)S-2 and symmetrical and unsymmetrical ditocopheryl sulfides (Toc)(2)S were simply prepared under remarkably mild conditions with complete control of the regiochemistry by using delta-, gamma-, and beta-tocopheryl-N-thiophthalimides (Toc-NSPht) as common starting materials. The roles of sulfur atom(s), H-bond and aryl ring substitution pattern on the antioxidant profile of these new compounds, which were assembled by linking together two tocopheryl units, are also discussed.