Journal of the Chemical Society. Perkin transactions I p. 3097 - 3100 (1981)
Update date:2022-08-16
Topics:
Mellor, John M.
Pons, B. Stanley
Stibbard, John H. A.
Electrochemical reduction of bridged 1,5-benzodiazepines, condensation products of o-phenylenediamines with 4,6-dimethylbicyclo<3.3.1>nona-3,6-diene-2,8-dione, has been studied.Cathodic acylation of 4,6-dimethyl-5,2,8-ethanylylidene-5H-1,9-benzodiazacycloundecene (2) in the presence of acetic anhydride affords the substituted barbaralane 5,11-diacetyl-8,9-dimethyl-8,5a,10a-ethanylylidene-8H-cycloheptaquinoxaline (6).Structures of the substituted barbaralanes have been established by 1H n.m.r. analysis at +100 deg C, at which temperature the complexities of conformational processes were avoided and the dominant valence isomers of the barbaralanes were recognised.At -2.35 V reduction proceeded in a single 2-electron wave.This behaviour is analogous to that of other Schiff bases and is contrasted with the electrochemical reduction of related heterocyclic systems.
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