Redox active donor-substituted punicin derivatives.
The redox active plant material punicin from Punica granatum, 2-hydroxy-1-(pyridinium-1-yl)-5-olate, and some derivatives were modified by substitution with 2-oxochromen-4-olate moieties to give donor-substituted molecules which form distinct types of atropisomeric mesomeric betaines and tetrapolar substances. Oxidation to new negatively-charged solvatochromic quinones was achieved on treatment of these betaines with CAN, taking advantage of the stabilizing properties of the electron-donating 2-oxochromen-4-olate partial structure. The quinones can be employed in model redox reactions. Cyclovoltametric studies have been performed.
Albrecht
Marcel
M
Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, Clausthal-Zellerfeld, Germany.
Schneider
Oliver
O
Schmidt
Andreas
A
D029561:Lythraceae / Q000737:chemistry*; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011726:Pyridinium Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
C540212:2-hydroxy-1-(pyridinium-1-yl)-5-olate; D011726:Pyridinium Compounds