Oxidation of aldehydes to acyl azides by chromic anhydride-azidotrimethylsilane

✍ Scribed by Jong Gun Lee; Ki Hoon Kwak

• Book ID: 104216225
• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 152 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79841-8

✦ Synopsis

Aldehydes are efJiciently oxidized fo acyl nzidcs by azidotrimetlzylsilanp and chromic anhydride nt room temperature (nromntic), or nt -10 'C (aliphatic).

Acyl azides are valuable synthetic intermediates.

They are not only useful for the preparation of amides, but also undergo a facile thermal rearrangement to alkyl isocyanates, from which amines, urethanes, ureas can be easily prepared'. Acyl azides are usually prepared from acid derivatives such as acyl chlorides and acyl hydrazines'.

Recently, there have been several reports on the application of the reagent combination of chromic anhydride-chlorotrfmethylsilane2.