ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Electrolytic Adamantylation by Reductive Coupling of Quinolinylhalides in the Presence of 1-BromoadamantaneElectrochemically generated anion radicals of a number of halogen-substituted quinolines 1 a-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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19813230305
Permalink
