A new redundant rearrangement of aromatic ring fused cyclic alpha-hydroxydithiane derivatives. Synthesis of aromatic ring fused cyclic 1,2-diketones with one-carbon ring expansion

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