Preparation of Labeled Aldehydes and Ketones from Enamides

✍ Scribed by Dr. Bernard T. Golding; Mr. Ah Kee Wong

• Publisher: John Wiley and Sons
• Year: 1981
• Tongue: English
• Weight: 232 KB
• Volume: 20
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.198100891

✦ Synopsis

Full exploitation of I70-NMR spectroscopy ['] in mechanistic organic chemistry requires efficient, simple methods for the synthesis of I70-labeled compounds. The classical method for labeling aldehydes and ketones with 1 7 0 or I8O is based on their reversible hydration['l. However, to obtain by this method aldehydes or ketones with the atom percentage of labeled oxygen approaching that of the water used, either a large excess of labeled water or repeated exchange is required. Several methods have been described in which an aldehyde or ketone is converted into a derivative which can be hydrolyzed with a stoichiometric amount of water. Suitable derivatives are a c e t a l ~l ~~, dithioketal~''~, and a m i n a l ~' ~~.