Silver oxide oxidation of an aldehyde with carbon tritium bonds vicinal to the carbonyl carbon

✍ Scribed by H. Paul Meloche; Claire T. Monti

• Publisher: Elsevier Science
• Year: 1975
• Tongue: English
• Weight: 220 KB
• Volume: 68
• Category: Article
• ISSN: 0003-2697
• DOI: 10.1016/0003-2697(75)90710-1

✦ Synopsis

The NH4OH-dependent silver oxide oxidation of D,L-[3-:~H~]malate semialdehyde-4-al to D,L-[3-3H~] malate was studied. A method is presented allowing carboxylate formation immediately subsequent to aldehyde generation by periodate cleavage. It was found that at high concentrations of AgzO, base-catalyzed detritiation of the semialdehyde is minimal, ranging 0.5~. The yield of malate appears to be quantitative. Thus, this method allows oxidation of an aldehyde to its carboxylate in high yield while preserving the configuration of the adjacent carbon atom.