ChemInform Abstract: Aryl (o-Phenylaryl) Thione S-Imides and S-Oxides. Intramolecular Cyclization and Subsequent Rearrangement.
Abstract
The aryl o-phenylaryl thioketones (I) react with the chloroamine salts (II) to form the intermediate S-imides (III) which produce a mixture of the fluorenesulfenamides (IV) and the compounds (V) - (VIII).
ChemInform Abstract
The aryl o-phenylaryl thioketones (I) react with the chloroamine salts (II) to form the intermediate S-imides (III) which produce a mixture of the fluorenesulfenamides (IV) and the compounds (V) - (VIII). Trapping of the intermediates (IIId) with methanol (IX) gives the α-methoxy derivatives (X). Oxidation of (I) with MCPBA yields the E- and Z-sulfines (XI) and (XII). The E-isomers (XI) cyclize upon treatment with aluminum trichloride and ethanol (XIII), forming the dibenzothiopyrans (XIV), whereas the Z-isomers (XII) only equilibrate with the E-forms (XI) under analogous conditions. (Intermediates).
