ISSN:
1434-193X
Keywords:
Electrochemistry
;
Regioselectivity
;
Solvent effects
;
o-Quinone imines
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
---The electrochemical reduction-Bamberger substitution of 2-nitroanisole in 1 M H2SO4 yields predominantly 2,5-dimethoxyaniline, not the expected 2,4-isomer. The selectivity was found to be acid- and solvent-dependent, with lower acidity and less polar solvents favoring the formation of 2,4-dimethoxyaniline during galvanostatic electrolysis. A mechanistic working hypothesis involving an ortho-quinone monoimine dication is presented to direct further synthetic studies.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
Permalink