TY - JOUR
T1 - Voltammetric behavior of β-phosphonylated nitroxide and its application to electrocatalytic oxidation of alcohol
AU - Kashiwagi, Yoshitomo
AU - Nishimura, Takuya
AU - Anzai, Jun ichi
N1 - Funding Information:
This work was supported in part by Grants-in-Aid for Scientific Research on Priority Areas (No. 11119208) and for Encouragement Research (No. 13750792) from the Ministry of Education, Culture, Sports, Science and Technology of Japan.
PY - 2002/2/1
Y1 - 2002/2/1
N2 - N-tert-Butyl-N-[1-diethylphosphono-(2,2-dimethylpropyl)]nitroxide (DEPN) as β-phosphonylated nitroxide was prepared using tert-butylamine, pivalaldehyde and phosphonic acid diethyl ether as starting materials. This nitroxide revealed a reversible redox peak in cyclic voltammetry at +0.81 V versus Ag/AgCl, and showed electrocatalysis for the oxidation of alcohol. A preparative electrocatalytic oxidation of 4-methylbenzyl alcohol on the nitroxide yielded 98% 4-methylbenzaldehyde by 10 h of electrolysis. The current efficiency, turnover number and pseudo-first-order kinetic constant of the reaction were 96.5%, 39 and 0.95 × 10-5 s-1, respectively.
AB - N-tert-Butyl-N-[1-diethylphosphono-(2,2-dimethylpropyl)]nitroxide (DEPN) as β-phosphonylated nitroxide was prepared using tert-butylamine, pivalaldehyde and phosphonic acid diethyl ether as starting materials. This nitroxide revealed a reversible redox peak in cyclic voltammetry at +0.81 V versus Ag/AgCl, and showed electrocatalysis for the oxidation of alcohol. A preparative electrocatalytic oxidation of 4-methylbenzyl alcohol on the nitroxide yielded 98% 4-methylbenzaldehyde by 10 h of electrolysis. The current efficiency, turnover number and pseudo-first-order kinetic constant of the reaction were 96.5%, 39 and 0.95 × 10-5 s-1, respectively.
KW - Alcohol
KW - Electrocatalytic oxidation
KW - Mediator
KW - β-Phosphonylated nitroxide
UR - http://www.scopus.com/inward/record.url?scp=0036472524&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0036472524&partnerID=8YFLogxK
U2 - 10.1016/S0013-4686(01)00843-X
DO - 10.1016/S0013-4686(01)00843-X
M3 - Article
AN - SCOPUS:0036472524
VL - 47
SP - 1317
EP - 1320
JO - Electrochimica Acta
JF - Electrochimica Acta
SN - 0013-4686
IS - 8
ER -