Studies on electrolytic substitution reactions. II. Anodic acetamidation, a novel anodic substitution reaction.

✍ Scribed by Lennart Eberson; Klas Nyberg

• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 205 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75664-4

✦ Synopsis

On tb basis of polarographic studies and preparative investigationa at controlled anode potentials lr2, we have previously postulated that anodie acetorylation of an organic substrate in acetic acid/acetate Ion proceeddi via an initial two-electron transfer from the substrate to the anode. The dlcationic intermediate reacts with acetate Ion to form a Whelan%type intermediate which leads to product by loss of a proton. Side-chain *etoxylation was observed for metblbenzenes *r3 , and thin ma&ion wan ala0 aamnm?d to occur via a dlcationdc species, which would fone a benzyl cation by loss of a proton from one of the metbyl groups. Rssulta and dlscusaio~ pertinent to this problem have been publitlhed Facently by 0-r aut,hora4. and It Is apparent that a mechanism involving cationic lntanmdiates ia an attractive pathway for a number of ancdlc processes. ife v&h to present t This work was supported by agrantfromthe Swedishl#atuml Science Research Council.