Electron beam-induced fries rearrangement of sulfonamide and sulfonate crystals

Kato, Jun*; Maekawa, Yasunari; Yoshida, Masaru

Chemistry Letters, 34(2), p.266 - 267, 2005/02

https://doi.org/10.1246/cl.2005.266

We have investigated the useful EB induced reactions of sulfonamide and sulfonate derivatives in the crystalline state. In this letter, we found that the EB sensitivity of sulfonic acid derivatives in the crystalline tate was much higher than that of the corresponding carboxylic acid derivatives, which was distinct from the results using other energy sources, to give Fries rearrangement products. It is notable that these reactions are solvent-free and are accompanied by the transformation of amide and ester linkages to hydrophilic aniline and phenol groups; especially, an acidic sulfonamide can be converted to the corresponding basic aniline derivatives. These new EB induced transformations can significantly contribute to designing new materials for EB lithography as well as nanoscopic architectures.