To probe the rearrangement ability of the aniline core a range of N(sp 2 )-sulfamated anilines were synthesised using TBSAB as a mild sulfamating agent (Chart 2) in 95-99% conversions and 70-99% isolated yield. The 2,6-dichloroaniline example (2g) proved recalcitrant to undergoing sulfamation under these conditions. Examples selected varied the steric bulk around the aniline nitrogen from hydrogen < methyl < ethyl < isopropyl. At this stage to avoid the complexity of simultaneous ortho product formation both ortho position were blocked except for 2c.