Stereochemistry of redox-demercuration of an optically active 8-(α-bromomercuriethyl)quinoline with zerovalent palladium complexes

A novel organomercurial bearing the metal atom at a chiral centre, 8-(α-bromomercuriethyl)quinoline (I) has been synthesized from the respective bromide and metallic mercury, and resolved via diastereomeric D-camphor sulphonates. Enantiomeric I has been treated with (Ph 3P) 4Pd 0 and (dba) 3Pd 2 0 t...

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Bibliographic Details
Published inJournal of organometallic chemistry Vol. 225; no. 1; pp. 57 - 61
Main Authors Sokolov, V.I., Bashilov, V.V., Musaev, A.A., Reutov, O.A.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.02.1982
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Summary:A novel organomercurial bearing the metal atom at a chiral centre, 8-(α-bromomercuriethyl)quinoline (I) has been synthesized from the respective bromide and metallic mercury, and resolved via diastereomeric D-camphor sulphonates. Enantiomeric I has been treated with (Ph 3P) 4Pd 0 and (dba) 3Pd 2 0 to give optically active chelate metallocycles II and III which had been previously known in racemic form. In both reactions, (-)I leads to (+)organopalladiums. The optical activity proves the heterolytic reaction mechanism.
ISSN:0022-328X
1872-8561
DOI:10.1016/S0022-328X(00)86810-2