Synlett 2005(17): 2667-2669  
DOI: 10.1055/s-2005-917104
LETTER
© Georg Thieme Verlag Stuttgart · New York

Facile Preparation of the Water-Soluble Singlet Oxygen Traps Anthracene-9,10-divinylsulfonate (AVS) and Anthracene-9,10-diethylsulfonate (AES) via a Heck Reaction with Vinylsulfonate

Véronique Nardello*a, Jean-Marie Aubrya, Peter Johnstonb, Ibrahim Buldukc, André H. M. de Vriesd, Paul L. Alsters*d
a LCOM, Équipe de Recherches ‘Oxydation & Formulation’, UMR CNRS 8009, ENSCL, BP 90108, 59652 Villeneuve d’Ascq Cedex, France
Fax: +33(3)20336369; e-Mail: veronique.rataj@univ-lille1.fr;
b Johnson-Matthey plc, Process Catalyst Development, Orchard Road, Royston, Hertfordshire SG8 5HE, UK
c Mercachem BV, P.O. Box 31070, 6503 CB Nijmegen, The Netherlands
d DSM Pharma Chemicals-Advanced Synthesis, Catalysis & Developments, P.O. Box 18, 6160 MD Geleen, The Netherlands
Further Information

Publication History

Received 27 July 2005
Publication Date:
05 October 2005 (online)

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Abstract

An easy 2-step method for the synthesis of the water-soluble singlet oxygen trap AES has been developed. The method is based on a novel Heck reaction with sodium vinylsulfonate followed by vinyl hydrogenation. It is shown that the Heck product AVS is also suitable as a water-soluble and colored singlet oxygen trap that allows singlet oxygen to be detected specifically and simply by visual inspection. The cumulative amount of 1O2 generated into the solution can be determined unambiguously by measuring the concentration of the endoperoxides AVSO2 or AESO2 by HPLC or by 1H NMR.