Uses
2-Trimethylsilylethanesulfonyl amide is a useful reagent for introduction of a SES-protected nitrogen functionality, which can be cleaved with fluoride ion.
Uses
2-(Trimethylsilyl)ethanesulfonamide is a source of nucleophilic nitrogen that can react in manifold
ways with electrophiles prior to removal of SES group with fluoride ion. It participates in the following reactions: Preparation of N-Sulfonylimines, Mitsunobu Reactions, Azaglycosylation Chemistry, Preparation of Sulfodiimides, Preparation of (N-SES-imino)phenyliodinane etc.
Preparation
2-(Trimethylsilyl)ethanesulfonamide is prepared by reaction of 2-(trimethylsilyl)
ethanesulfonyl chloride (accessible from the commercially
available sodium salt of the corresponding sulfonic acid or starting
from vinyl trimethylsilane) with gaseous ammonia (eq 1).
