88205-40-7Relevant academic research and scientific papers
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.
