Mercuriation and thalliation of polystyrene: conversion of the products into polystyrenes containing lodobenzene, phenylboronic acid, and phenol residues

Abstract

Linear and 1% crosslinked polystyrenes were mercuriated and thalliated. Treatment of the mercuriated products with iodine and the thalliated products with potassium iodide gave iodinated polystyrenes. The metallated polymers reacted with borane to give polymer-supported arylboranes, and these on treatment with water gave polystyrenes containing phenylboronic acid residues. The latter can be used as polymer-supported protecting groups for diols. Oxidation of the polymers containing phenylboronic acid residues with trimethylamine oxide or with alkaline hydrogen peroxide gave polymers containing phenol residues.