Trichlorophenol (TCP) sulfonate esters: a selective alternative to pentafluorophenol (PFP) esters and sulfonyl chlorides for the preparation of sulfonamides

Jonathan D Wilden; Lynsey Geldeard; Chieh C Lee; Duncan B Judd; Stephen Caddick

doi:10.1039/b614604j

Trichlorophenol (TCP) sulfonate esters: a selective alternative to pentafluorophenol (PFP) esters and sulfonyl chlorides for the preparation of sulfonamides

Chem Commun (Camb). 2007 Mar 14:(10):1074-6. doi: 10.1039/b614604j. Epub 2006 Dec 21.

Authors

Jonathan D Wilden¹, Lynsey Geldeard, Chieh C Lee, Duncan B Judd, Stephen Caddick

Affiliation

¹ The Christopher Ingold Laboratories, Department of Chemistry, University College London, 20 Gordon Street, London, UKWC1H 0AJ. j.wilden@ucl.ac.uk

PMID: 17325810
DOI: 10.1039/b614604j

Abstract

2,4,6-Trichlorophenol (TCP) sulfonate esters undergo effective aminolysis under conventional heating and microwave irradiation; the reactivity of these species is such that chemoselective transformations of PFP sulfonate esters can be achieved.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chlorophenols / chemistry*
Chlorophenols / metabolism
Esters / chemical synthesis*
Esters / chemistry
Fluorobenzenes / chemistry*
Molecular Structure
Phenols / chemistry*
Sulfinic Acids / chemistry*
Sulfonamides / chemical synthesis*
Sulfonic Acids / chemistry*
Sulfonic Acids / metabolism

Substances

Chlorophenols
Esters
Fluorobenzenes
Phenols
Sulfinic Acids
Sulfonamides
Sulfonic Acids
sulfonyl chloride
2,3,4,5,6-pentafluorophenol
2,4,6-trichlorophenol