Radical Mediated Oxidations in Organic Chemistry; 1. Direct Oxidation of Benzylic Silyl Ethers to Carbonyl Compounds and Primary Aliphatic Silyl Ethers to Simple Esters

Abstract

Benzylic trimethylsilyl ethers are directly oxidised to aromatic aldehydes using N-bromosuccinimide in the presence of a catalytic amount to 2,2′-azobisisobutyronitrile. Aliphatic primary trimethylsilyl ethers yield simple esters directly formed from two molecular equivalents of the starting trimethylsilyl ethers rather than the expected aliphatic aldehydes.