Oxidation of organic compounds with cerium(IV). IX. Formation of 2-methyltetrahydrofuran by oxidation of 1-pentanol

✍ Scribed by Walter S. Trahanovsky; Marian Gordon Young; Paul M. Nave

• Book ID: 104239877
• Publisher: Elsevier Science
• Year: 1969
• Tongue: French
• Weight: 183 KB
• Volume: 10
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)88551-8

✦ Synopsis

Although benzyl alcohols (2,3) and cyclopropanemethanol (4) are converted to the corresponding aldehydes in nearly quantitative yield by the oxidation with ceric ammonium nitrate (CAN), we have found that many other alcohols undergo a cleavage reaction when oxidized with CAN (1,5). In this communication we wish to report that the CAN oxidation of a typical primary aliphatic alcohol, 1-pentanol, gives the corresponding tetrahydrofuran as the major neutral product and only traces of the corresponding aldehyde. Tetrahydrofuran formation is thus the third type of reaction that alcohols undergo when oxidized with CAN.