Fluoride ion promoted anodic substitutions of chalcogeno compounds.2. Regioselective anodic methoxylation of 1,1-dihydro-perfluoroalkyl and cyanomethyl selenides.

✍ Scribed by Kazimierz Surowiec; Toshio Fuchigami

• Book ID: 104224930
• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 247 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)91862-8

✦ Synopsis

Anodic methoxylation of 1,1-dihydroperfluoroalkyl and cyanomethyl selenides was achieved in the presence of Et3N-3HF as a supporting electrolyte. Anodic a -functionalization of amines and arenes is well-established.3~4) However, such functionalization of other heteroatom compounds has been undeveloped. Recently, we have found that anodic a-methoxylation of sulfides was markedly promoted by strong electron-withdrawing groups such as perfluoroalkyl gro~ps.~") The reaction is noticeable because nucleophilic substitution at the position (r to the perfluoroalkyl group is usually quite diflicult to achieve.@