95793-70-7Relevant articles and documents
Possibilities and Limits of the Carbanionically Induced Sulfonamide-Aminosulfone Rearrangement
Hellwinkel, Dieter,Lenz, Ruediger
, p. 66 - 85 (2007/10/02)
When transfering the title reaction to the 2- and 1-naphthyltoluenesulfonamides 5 and 10, the -shift of the arylsulfonyl group proceeds into the 3- and 2-position (to give 9 and 12, respectively), which is in full compliance with optimal conjugative and steric conditions for the relevant intermediates 8 and 11.Attemps to initiate comparable -rearrangements through the o-lithiated biphenyl derivative 17 and the p-lithiated N-phenyltoluenesulfonamide 23 led again, after extended transmetalation cascades, to the conventional -rearrangement products 22 and 32, respectively.In attempting to cause in the o-tolylbenzenesulfonamide 49 an anionically induced -sulfonyl shift into the benzyl position, two fragments of the starting molecule combined to give the novel heteropolycycle 51.Finally, it could be shown that contrary to the literature, the sulfonamides 46 and 57 rearrange also photolytically to the o-aminosulfones 45 and 58.
