ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Electrochemical Reductive Alkylation of Azomethines with 1-Bromadamantane and 9-Bromo-tetrahydro-exo-dicyclopentadieneElectrochemically 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-[α-(aryl- or alkylamino)-α-arylmethyl]-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.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19863280103
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