Stereospecific Oxidation of Alkenes by Iodine Tris(trifluoroacetate)

✍ Scribed by Priv.-Doz. Dr. Joachim Buddrus

• Book ID: 101545968
• Publisher: John Wiley and Sons
• Year: 1973
• Tongue: English
• Weight: 197 KB
• Volume: 12
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.197301631

✦ Synopsis

We have now prepared the ozonide (4), which appears to be an ideal starting material for the synthesis of (2). Compound ( 4 ) [m.p. 142°C; NMR (CCl,): ~= 8 . 6 0 (6H), 8.73 (3H), 8.77 (3H), 9.07 (6H), 9.20 (6H)] is formed surprisingly smoothly by the action of AgBF, on the valence-isomeric ozonide (3) 13]. Reducing (4) with triphenylphosphane affords the diacetyl compound, m. p. 179 "C, containing an intact bicyclobutane ring skeleton. Irradiation of ( 4 ) at room temperature or -70°C effects fission into hexamethylbenzene and acetic anhydride.