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Synthesis 2003(8): 1225-1230
DOI: 10.1055/s-2003-39413
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Improved, General Procedure to S-Aryl Thiol Esters: A New Synthetic Application of Dry Arenediazonium o-Benzenedisulfonimides

Margherita Barbero, Iacopo Degani, Stefano Dughera*, Rita Fochi*
Dip.to di Chimica Generale ed Organica Applicata dell’Università, C.so M. D’Azeglio 48, 10125 Torino, Italy
e-Mail: rita.fochi@unito.it;
Further Information

Publication History

Received 11 March 2003
Publication Date:
26 May 2003 (online)

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Abstract

The reaction between dry arenediazonium o-benzenedi­sulfonimides (1) and sodium thioacetate or thiobenzoate in anhydrous acetonitrile at room temperature is an efficient and safe procedure, of general validity, for the preparation of S-aryl thiol esters. The products can be easily purified and the yields are always very high. Of the 28 considered examples, the average yield of the S-aryl thioacetates (7) was 86% and that of the S-aryl thiobenzoates (8) 88%. It was possible to recover, in good amount and from all the reactions, o-benzenedisulfonimide (9), reusable for the preparation of salts 1.

Key words

thiol esters - diazonium compounds - sulfur

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