Cycloaddition reactions of sodium dinitroxytrioxide (Angeli's salt)

✍ Scribed by Lokman Torun; Taj Mohammad; Harry Morrison

• Book ID: 104261745
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 182 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00962-4

✦ Synopsis

Angeli's salt undergoes a quantitative reaction with 1,3-diphenylisobenzofuran in a methanol/water solution at room temperature to give a product (1) explicable by an initial [4+2] cycloaddition reaction. Under the same conditions, Angeli's salt reacts with 1-naphthaldehyde to give 1-naphthoic acid in good yield. This reaction can also be explained by an initial [2+2] cycloaddition to give a hydroxamic acid, which is then hydrolyzed to the carboxylic acid.