Synthesis of Aromatic Disulfonic Acids for Water-Soluble Dibenzo­thiophene Derivatives

Abstract There is a need for efficient methods for the synthesis of water-soluble dibenzothiophene (DBT) and dibenzothiophene S -oxide (DBTO) derivatives to allow for the study of atomic oxygen in biological applications. Attaining water-solubility of aromatic compounds is effectively achieved throu...

Full description

Saved in:
Bibliographic Details
Published in:Synthesis (Stuttgart) 2018-06, Vol.50 (12), p.2359-2366
Main Authors: Omlid, Sara M., Isor, Ankita, Sulkowski, Kathryn L., Chintala, S. M., Petroff, John T., McCulla, Ryan D.
Format: Article
Language:English
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Abstract There is a need for efficient methods for the synthesis of water-soluble dibenzothiophene (DBT) and dibenzothiophene S -oxide (DBTO) derivatives to allow for the study of atomic oxygen in biological applications. Attaining water-solubility of aromatic compounds is effectively achieved through functionalization with sulfonic acid groups. Three approaches for the synthesis were considered. An indirect approach was unsuccessful. A modular approach was found to be highly effective for one DBTO disulfonic acid derivative (>99% pure). The direct approach was the most straightforward and highest-yielding route. Additionally, a highly effective, scalable, and improved purification method was identified for disulfonic acid DBT and DBTO derivatives, allowing for the isolation of positional isomers and other modifications by using reverse-phase high-performance flash chromatography.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1591969