144688-80-2Relevant academic research and scientific papers
Distannane mediated reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving radical addition followed by electron transfer
Maruyama, Tomokazu,Suga, Seiji,Yoshida, Jun-ichi
, p. 6519 - 6525 (2006)
Hexabutyldistannane was found to be an effective mediator allowing the reaction of N-acyliminium ion pools with alkyl halides. A chain mechanism involving the addition of an alkyl radical generated from an alkyl halide to an N-acyliminium ion followed by the one-electron reduction of the resulting radical-cation by distannane was proposed.
Radical addition to cation pool . Reverse process of radical cation fragmentation
Maruyama, Tomokazu,Suga, Seiji,Yoshida, Jun-Ichi
, p. 7324 - 7325 (2005)
The reaction of an N-acyliminium ion with an alkyl iodide and hexabutyldistannane took place to give the alkylation product. A mechanism involving the addition of an alkyl radical to an N-acyliminium ion to produce the corresponding radical cation has been suggested. Copyright
Electrochemical deallylation of α-allyl cyclic amines and synthesis of optically active quaternary cyclic amino acids
Kirira, Peter G.,Kuriyama, Masami,Onomura, Osamu
experimental part, p. 3970 - 3982 (2010/07/04)
Electrochemical oxidation of α-allylated and α-betizylated N-acylated cyclic amines by using a graphite anode easily affords the corresponding α-methoxylated products with up to 76% yield. Ease of oxidation was affected by the type of electrode, the size
Reactions of a N-acyliminium ion pool with benzylsilanes. Implication of a radical/cation/radical cation chain mechanism involving oxidative C-Si bond cleavage
Maruyama, Tomokazu,Mizuno, Yusuke,Shimizu, Ikuo,Suga, Seiji,Yoshida, Jun-Ichi
, p. 1902 - 1903 (2007/10/03)
The reaction of a N-acyliminium ion pool with benzylsilane proceeds by a chain mechanism involving oxidative C-Si bond cleavage. A radical/cation/radical cation crossover mechanism involving single electron transfer has been proposed. The effective binary
Reaction of an electrogenerated 'iminium cation pool' with organometallic reagents. Direct oxidative α-alkylation and -arylation of amine derivatives
Suga, Seiji,Okajima, Masayuki,Yoshida, Jun-ichi
, p. 2173 - 2176 (2007/10/03)
We have developed an efficient direct oxidative α-alkylation and -arylation of carbamates based on the 'cation pool' method. Grignard reagents, organozinc compounds, and organoaluminum compounds are effective as carbon nucleophiles toward iminium cation pools generated by low temperature electrolysis of carbamates.
Electroorganic chemistry 139. Electroreductive decyanation of nitriles and its application to synthesis of α-alkylamines
Shono, Tatsuya,Terauchi, Jun,Kitayama, Kenji,Takeshima, Yo-Ichiro,Masumura, Yoshihiro
, p. 8253 - 8262 (2007/10/02)
Electroreduction of nitriles gave the corresponding decyanated products when Zn was used as the material of cathode in aprotic solvent (DMF or MeCN) containing Et4NOTs as a supporting electrolyte. Alkylation of amines at the α-position was effectively achieved by cyanation of amines at the α-position, and α-alkylation of the resultant α-amino nitriles followed by the electroreductive decyanation.
