Thermal rearrangement of some benzoin arylsulfonylhydrazone derivatives

✍ Scribed by Abd El-Aal M. Gaber; Omima S. Mohamed; Morsy M. Aly

• Book ID: 104019239
• Publisher: Elsevier Science
• Year: 2005
• Tongue: English
• Weight: 273 KB
• Volume: 73
• Category: Article
• ISSN: 0165-2370
• DOI: 10.1016/j.jaap.2004.09.004

✦ Synopsis

Thermolysis of benzoin benzenep-sulfonylhydrazone I in nitrogen atmosphere at 200 8C leads to the formation of numerous products among which the following were identified: ammonia, benzoic acid, benzophenone, benzil, aniline, diphenyl acetylene, deoxybenzoin, Nbenzylbenzamide, diphenyldisulfide, diphenylthiosulfone, S-phenylthiobenzoate, benzenesulfonamide, 2-phenylindole, 2,3,4,5-tetraphenylfuran, 2,4,5-triphenylimidazole, and 2,4,5-triphenyloxazole. Similarly, thermolysis of I in the presence of isoquinoline as a radical trap under the same conditions gave 1-phenylisoquioline in addition to the previously mentioned products. Analogous results were also obtained for thermolysis of benzoin toluenep-sulfonylhydrazone II. The formation of such products which implies the homolysis of different bonds in the benzoin derivatives followed by reaction of the so formed radicals.