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Electrochemical and photoelectronic spectral study of compounds with high ionization potentials: Anodic oxidation of vinyl triflates in aprotic solvents
Author(s) -
Kowalski Mark H.,
Pons Joseph W.,
Stang Peter J.,
Pons Stanley,
Werstiuk N. H.,
Ashley Kevin
Publication year - 1990
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610031008
Subject(s) - chemistry , ultramicroelectrode , electrochemistry , cyclic voltammetry , redox , electrode , electrolyte , trifluoromethanesulfonate , inorganic chemistry , analytical chemistry (journal) , photochemistry , organic chemistry , catalysis
Microelectrodes can be used to measure redox half‐wave potentials in aprotic solvents containing no purposely added supporting electrolyte. By employing an electrode of sufficiently small size, the accessible potential range in solution is considerably extended. The electrochemical oxidation of vinyl (enol) triflates, which are oxidized at high electrode potentials, can therefore be studied using an ultramicroelectrode. Oxidation and ionization potentials, determined by ultramicroelectrode voltammetry and He I photoelectron spectroscopy, respectively, of 2‐methylprop‐1‐enyl, cyclohexenyl, cyclopentenyl, 1,1‐diphenylethenyl and prop‐2‐enyl triflate are reported. The results from electrochemical measurements and photoelectron spectra were compared.