The novel benziodazole oxides (3) can be prepared by oxidation of the readily available 2-iodobenzamides (5 or 6) with potassium bromate. Benziodazole oxides can find practical application as selective oxidizing reagents analogous to the widely used Dess-Martin periodinane (1) and benziodoxole oxide (2). Preliminary results indicate that reagents 3 can oxidize primary alcohols to aldehydes, while non-symmetric sulfides are oxidized to chiral sulfoxides with moderate enantioselectivity.
Bibliographical noteFunding Information:
This work was supported by a research grant from the National Science Foundation (NSF/CHE-9802823). We would also like to thank the Minnesota Supercomputer Institute and the UMD Digital Imaging Laboratory (DIL) for a generous allocation of computer resources.