88205-32-7Relevant articles and documents
Electrochemical Oxidation of Aromatic Ethers. Part 8. Evidence of Homogeneous Electron Transfer during the 'Low Potential' Oxidation of Laudanosine
Hutchins, Michael,Sainsbury, Malcolm,Scopes, David I. C.
, p. 2059 - 2064 (2007/10/02)
Photolysis of N-amino- and N-nitroso-derivatives of 1,2,3,4-tetrahydropapaverine fails to produce aryl-aryl coupled products analogous to O-methylflavinantine.Instead both the 1- and 2-substituents of the heterocyclic ring are cleaved to give 6,7-dimethoxy-3,4-dihydroisoquinolines and veratraldehyde, the latter being an oxidation product of the 3,4-dimethoxybenzyl radical and/or cation.From this evidence, and the results of an electrolysis experiment carried out at high dilution, it is considered that the anodic cyclisation of laudanosine to O-methylflavinantine proceeds through homogeneous electron transfer rather than via homoconjugative activation within the intermediate radical cation as proposed by other workers.