Anodic oxidation of substituted methoxyphenols. Mass spectrometric identification of methanol formed

✍ Scribed by M. Petek; Stanley Bruckenstein; B. Feinberg; Ralph N. Adams

• Book ID: 104149496
• Publisher: Elsevier Science
• Year: 1973
• Weight: 261 KB
• Volume: 42
• Category: Article
• ISSN: 0022-0728
• DOI: 10.1016/s0022-0728(73)80328-6

✦ Synopsis

The anodic oxidation of substituted methoxyphenols is of great interest as a model of biosynthetic pathways in the natural product field 1'2. Several excellent examples of the electro-preparation of natural products and intermediates have recently been given 3'4. Little attention has been given to these reactions at the voltammetric and mechanistic level with the exception of Hawley's study of the p-methoxyphenol oxidation 5.

We have been particularly interested in the anodic demethoxylation of the 3-methoxycatecholamines which occur as metabolites of the neurotransmitters dopamine and norepinephrine. A summary of the oxidative demethoxylation of these and related compounds is given herein. The elegant features of the "mass spectrometer electrode" for detecting volatile products of electrode reactions was utilized in a cooperative study to define unequivocally the reaction scheme.

The structures of the compounds studied are shown in Table