Electrochemical oxidation of acylsilanes

✍ Scribed by Jun-ichi Yoshida; Shin-ichiro Matsunaga; Sachihiko Isoe

• Book ID: 104244851
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 274 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93768-2

✦ Synopsis

Oxidation potentials of acylsilanes were found to be much less than those of the corresponding ketones and aldehydes. Electrochemical oxidation of acylsilanes resulted in facile cleavage of the carbon-silicon bond and introduction of oxygen and nitrogen nucleophiles at the carbonyl carbon. Therefore acylsilanes serve as a synthetic equivalent of acyl cations.

We have been investigating the electrochemical oxidation of silicon substituted heteroatom compounds2 and reported that substitution of a silyl group at the carbon adjacent to the oxygen resulted in significant decrease in oxidation p0tentials.S The electrochemical oxidation of silicon substituted ethers took place smoothly to cleave