79754-19-1Relevant academic research and scientific papers
Direct and indirect electrochemical generation of alkoxycarbenium ion pools from thioacetals
Matsumoto, Kouichi,Ueoka, Koji,Suzuki, Shinkiti,Suga, Seiji,Yoshida, Jun-ichi
, p. 10901 - 10907 (2009)
Thioacetals were found to be effective precursors to generate and accumulate alkoxycarbenium ions based on direct and indirect cation pool methods. Alkoxycarbenium ions thus generated reacted with carbon nucleophiles such as allylsilanes and enol silyl et
Indirect cation pool method. Rapid generation of alkoxycarbenium ion pools from thioacetals
Suga, Seiji,Matsumoto, Kouichi,Ueoka, Koji,Yoshida, Jun-Ichi
, p. 7710 - 7711 (2007/10/03)
A sequential one-pot indirect cation pool method has been developed. The method involves the electrochemical generation and accumulation of ArS(ArSSAr)+ at low temperature (step 1) and the follow-up reaction with a thioacetal to generate an alk
Electrooxidative Inter- and Intramolecular Carbon-Carbon Bond Formation Using Organothio Groups as Electroauxiliaries
Yoshida, Jun-Ichi,Sugawara, Masanobu,Tatsumi, Masao,Rise, Naoki
, p. 5950 - 5961 (2007/10/03)
The introduction of an organothio group to an α-carbon of ethers results in significant decrease of the oxidation potentials. Anodic oxidation of α-organothioethers gives rise to facile cleavage of the C-S bond and the introduction of carbon nucleophiles on the carbon. Allylsilanes, silyl enol ethers, and trimethylsilyl cyanide serve as effective carbon nucleophiles. The anodic oxidation of the α-organothioethers having a carbon-carbon double bond in an appropriate position using Bu4-NBF4 as the supporting electrolyte leads to the effective cyclization and the introduction of the fluoride to one of the formal olefinic carbon. The present study demonstrates the effectiveness of organothio groups as electroauxiliaries in electrooxidative inter- and intramolecular carbon-carbon bond formation.
