Sodium borohydride in an acetonitrile medium: An efficient reagent for reductive Beckmann type fragmentation of α-amino oximes

✍ Scribed by Pavel A. Petukhov; Alexey V. Tkachev

• Book ID: 104207497
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 948 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01142-8

✦ Synopsis

When treated with sodium borohydride in boiling acetonitril¢, cx-amino oximes are transformed to the corresponding ¢0-anuno nitriles in 31-87% yield. Easily available a-amino oximes with cyclohexane, methylcyclohaxene, p-menthane, carane, pinane, and caryophyllane carbon skeletons are tested. The reaction was found to proceed only in an aliphatic nitrile medium; the specific role of a nitrile is discussed. Beckmann synchronous mechanism was confirmed for the fragmentation stage followed by reduction of the intermediate immonium salt.