A Simple Preparation of Aryl Methanesulfonates by Thermal Decomposition of Dry Arenediazonium o-Benzenedisulfonimides in Methanesulfonic Acid

Margherita Barbero; Iacopo Degani; Stefano Dughera; Rita Fochi; Paolo Perracino

doi:10.1055/s-1999-3696

Synthesis 1999; 1999(1): 90-93
DOI: 10.1055/s-1999-3696

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A Simple Preparation of Aryl Methanesulfonates by Thermal Decomposition of Dry Arenediazonium o-Benzenedisulfonimides in Methanesulfonic Acid

Margherita Barbero^* , Iacopo Degani, Stefano Dughera, Rita Fochi, Paolo Perracino

^*Dipartimento di Chimica Generale ed Organica Applicata, Università di Torino, C.so M. D'Azeglio 48, I-10125 Torino, Italy; Fax +39(11)6 70 76 42; E-mail: fochi@silver.ch.unito.it

Abstract

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Aryl methanesulfonates 3 (18 examples) were easily prepared by thermal decomposition of dry arenediazonium o-benzene-disulfonimides 1 in methanesulfonic acid (2). The reactions were carried out at temperatures between 60 and 120 °C for times between 0.5 and 8 h. The aryl methanesulfonates were obtained in reproducible yield of 70-90%, with few exceptions. In all cases the o-benzenedisulfonimide (4) could be recovered in good yields which can then be reused to prepare the salts 1. When thermal decomposition of salts 1 was carried out in trifluoromethanesulfonic acid (5) at 90-120 °C for 1-2 h, aryl trifluoromethanesulfonates 6 were obtained in 73-78% yield (3 examples).

stable dry arenediazonium salts - aryl methanesulfonates - aryl trifluoromethanesulfonates - o-benzenedisulfonimide

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