89516-06-3Relevant academic research and scientific papers
Electrochemical Reductive Alkylation of Azomethines with 1-Bromadamantane and 9-Bromo-tetrahydro-exo-dicyclopentadiene
Hess, U.,Lieberenz, C.,Feuerherd, B.
, p. 7 - 20 (2007/10/02)
Electrochemically generated radical anions of Schiffbases 1a-11 react in DMF and in the presence of bridgeheadhalogenides as 1-bromoadamantane and 9-bromo-tetrahydro-exo-dicyclopentadiene to 1--adamantanes and the correspondent 9-tetrahydro-exo-dicyclopentadienes.In the course of SET-mechanism originating bridgehead radicals couple with the azomethine-radicalanions at the position of the highest unpaired electron density, which is predominantly the carbon of the C,N-double bond.Only in cases when this density at the N-atom is relatively high, or steric hindrance impedes C-alkylation, N-hydroalkylated products as N,N-disubstituted 1-aminoadamantanes and 9-amino-tetrahydro-exo-dicyclopentadienes are formed.Product distribution, cyclic-voltammetric results and quantumchemical data are discussed in terms of mechanism.
