- Electrolytic Adamantylation by Reductive Coupling of Quinolinylhalides in the Presence of 1-Bromoadamantane
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Electrochemically generated anion radicals of a number of halogen-substituted quinolines 1a-g dehalogenate in N,N-dimethylformamide to halogen anions and radicals, which may stabilize by hydrogen abstraction from the solvent.In the presence of 1-bromoadamantane the fragments of reductive dehalogenation may be used synthetically for indirect generation of 1-bromoadamantane-radicals, which react predominantly to cross-coupled 2- and 7-monoadamantylated dihydroquinoline- and quinoline-structures, independent of the original halogen position.If C-2 is blocked, adamantylation takes place in the carbocyclic ring.Product distribution and cyclic-voltammetric results are discussed in terms of mechanism.
- Hess, U.,Huhn, D.
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p. 381 - 392
(2007/10/02)
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