Selective deprotection of phenolic polysulfonates

Abstract

Nosylates of phenols can be selectively deprotected by thiocresol anions in DMSO. Successful deprotection can be accomplished in molecules containing aryl-appended halides, ethers, aldehydes, alkanesulfonates or arylsulfonates. Nosylate deprotection is accomplished by the CS bond rupture which is believed to proceed by nucleophilic aromatic substitution.

Keywords:

• sulfonate deprotection
• phenols
• CS cleavage of p-nitrobenzenesulfonates
• nucleophilic aromatic substitutions
• single-electron transfer

Acknowledgements

The authors gratefully acknowledge technical assistance from D. Durant, R. Smith and B. McNally.