A New Redundant Rearrangement of Aromatic Ring Fused Cyclic α-Hydroxydithiane Derivatives. Synthesis of Aromatic Ring Fused Cyclic 1,2-Diketones with One-Carbon Ring Expansion

Article abstract of DOI:10.1021/jo990634s

A new reaction involving rearrangement of aromatic ring fused cyclic dithiane alcohol by N-chlorosuccinimide in CH₂Cl₂-H₂O to the corresponding one-carbon ring expanded 1,2-diketone has been developed. A wide range of structurally varied dithiane alcohols have been found to undergo this rearrangement in high yields. The general criteria and reaction mechanism for this rearrangement have also been worked out.