Synthesis of Vinyl Sulfones by Ring Opening of 4,4-Dioxo-2,3-dihydrobenzo[b][1,4]oxathiines and Their In Situ Reactions with Nucleophilic or Electrophilic Agents

摘要

A new, mild method of synthesis of 2-hydroxyphenyl vinyl sulfones from 4,4-dioxo-2,3-dihydrobenzo[b][1,4]oxathiine derivatives is described. The products were further modified in situ, either by Michael addition of nucleophiles or by reaction of the 2-hydroxy group with an electrophile. The method can be utilized to immobilize proteins on a suitable support, or for other similar applications, as generation of the vinyl sulfone is always accompanied by formation of phenolate anion that can be used to bond in situ the vinyl sulfone to a suitable support.