REACTION OF POLYMERIZATION-RESISTANT 1,2-DITHIOLANES WITH SULFOXONIUM YLIDES. NEW METHOD FOR 1,3-DITHIANE SYNTHESIS

Abstract

Reaction of polymerization-resistant 1,2-dithiolanes 1 with dimethylsulfoxonium methylide 3 was developed for the synthesis of the corresponding 1,3-dithianes 4 by a high-dilution method. Oxygen did not prevent the formation of 4, but facilitated the product separation leading to a good yield and the excellent purity of 4.

Key Words:

• 1,2-Dithiolanes
• nucleophilic S‒S bond cleavage
• sulfoxonium ylide
• methylene insertion of cyclic disulfides
• 1,3-dithiane formation