REACTION OF POLYMERIZATION-RESISTANT 1,2-DITHIOLANES WITH SULFONIUM YLIDES

Abstract Reaction of the polymerization resistant 1,2-dithiolane 1 with sulfonium ylides 2 was examined in relation to coenzyme lipoic acid. The strained cyclic disulfide 1 was highly reactive towards stabilized carbanions 2 to give the corresponding ring-opened products, which further reacted to give the 1,3-dithiane 4 and the 1,3-dithianyl sulfide 5. The 1,3-dithiane formation was nearly quantitative when the ylide from benzyldimethylsulfonium was used.