Journal of the Chemical Society. Perkin transactions I p. 2059 - 2064 (1983)
Update date:2022-08-05
Topics:
Hutchins, Michael
Sainsbury, Malcolm
Scopes, David I. C.
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.
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