Premium
The difference between the reactivities of azomethine bonds in metamitron in electrochemical and chemical reductions
Author(s) -
Riedl František,
Ludvík Jiří,
Liška František,
Zuman Petr
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330683
Subject(s) - chemistry , double bond , protonation , electrochemistry , borohydride , bond strength , aqueous solution , triple bond , bond order , organic chemistry , bond length , molecule , catalysis , electrode , adhesive , ion , layer (electronics)
Electrochemical reduction of a herbicide metamitron (4‐amino‐3‐mefhyl‐6‐phenyl‐1,2,4‐triazin‐5(4 H )‐one) in buffered aqueous solutions occurs on the protonated 1,6‐carbon‐nitrogen double bond. The 2,3‐double bond in the resulting 1,6‐dihydrometamitron is electrochemically reduced at considerably more negative potentials. In reaction with borohydride the 2,3‐double bond is reduced first. Reduction of the 1,6‐double bond is very little influenced by replacing the 2,3‐double bond by the ‐NHCH‐ grouping in 2,3‐dihydrometamitron.