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

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