ChemInform Abstract: ortho-Directed Metallation in the Regiocontrolled Synthesis of Enantiopure 2- and/or 3-Substituted (S)S-(p-Tolylsulfinyl)-1,4- benzoquinones.

✍ Scribed by M. C. CARRENO; J. L. GARCIA RUANO; M. A. TOLEDO; A. URBANO

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199731094

✦ Synopsis

1997 sulfoxides, sulfones, sulfenes and derivatives sulfoxides, sulfones, sulfenes and derivatives (benzene compounds) Q 0600 31 -094 ortho-Directed Metallation in the Regiocontrolled Synthesis of Enantiopure 2-and/or 3-Substituted (S)S-(p-Tolylsulfinyl)-1,4-benzoquinones.

-It is shown that the dimethylhydroquinones (I) undergo regioselective lithiation yielding predominantly sulfoxides of type (III) after sulfinylation (83-55% yield of (IIIb)-(IIIe)). The bromoderivatives ( VI) and (VII) give sulfoxides of type (III) or regioisomers like (IV) depending on the position of bromine. Subsequent oxidation leads to title compounds such as (V).