Synthesis and reactivity of polydisulfonimides.
The first synthesis of alkyl disulfonimide oligomers is presented. In the process of synthesizing these oligomers, previously unreported reactivity of the N-substituted disulfonimide functional group was discovered. Under basic conditions, unexpected lengthening of the oligomers occurs through a "transdisulfonimidation" reaction, whereby new disulfonimides are synthesized from existing ones by reaction with sulfonamide anion. This process appears to proceed via formation of a sulfene intermediate. Support for the E1cB(Rev) mechanism includes isotope scrambling, substituent effects, and sulfene trapping.
Burlingham
B T
BT
Department of Chemistry, Indiana University, Bloomington, IN 47405, USA.
Widlanski
T S
TS
D007094:Imides / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry
D007094:Imides; D013450:Sulfones