Synthesis of sulfonimide-based dendrimers and dendrons possessing mixed 1 → 2 and 1 → 4 branching motifs

Abstract The synthesis of dendrimers and a chlorosulfo-dendron possessing a unique combination of 1 → 2 and 1 → 4 branching types is described. The procedure consists of a two-step preparation of 3,5-dinitrobenzene-1-sulfonyl chloride, which was used for the persulfonylation of p -toluidine and 4-(benzylthio)aniline. The obtained tetranitro compounds were reduced to the corresponding tetraamines. The latter were decorated with eight 4-toluene sulfonyl groups each to furnish the corresponding dendrimers. Oxidation of the dendrimer possessing a 4-(benzylthio)phenylene core with N -chlorosuccinimide resulted in the formation of a dendron with a sulfonyl chloride functionality at the focal point.