Reaction of silyl enol ethers with N-chlorosuccinimide: trapping of the siloxycarbinyl cation by an azide anion
Abstract
Reaction of silyl enol ethers (1a–f) with N-chlorosuccinimide afforded siloxycarbinyl cations which were trapped by nucleophiles (NaN3 and MeOH); subsequent rearrangement of the azido products (2a,b,d,e–N3) under reflux in decalin led to anilide derivatives (3a,b,d,e).