Electro-organic reactions—14. The intramolecular cathodic cyclization of abscisic acid methyl ester

✍ Scribed by Bulent Terem; James H.P. Utley

• Publisher: Elsevier Science
• Year: 1979
• Tongue: English
• Weight: 365 KB
• Volume: 24
• Category: Article
• ISSN: 0013-4686
• DOI: 10.1016/0013-4686(79)85004-5

✦ Synopsis

Abs&act -Abscisic acid methyl ester (1) is reduced smoothly at controlled potential at a mercury cathode in a 2 F mol-' reaction which gives the bicyclic ester (5) in good yield. Cyclic voltammetry of (1). and several related model compounds, reveals that the C-6 hydroxyl group precludes conjugation throughout the molecule and thereby allows sk.ctive electron transfer to the side chain. The radical-anion so formed isomeriscs and undergoes rapid bcxo-trig cyclization.