Re-evaluation of Organocuprate Reactivity: Logarithmic Reactivity Profiles for Iodo- versus Cyano-Gilman Reagents in the Reactions of Organocuprates with 2-Cyclohexenone and Iodocyclohexane

The differences in reactivity between iodo‐Gilman reagents R2CuLi⋅LiI and cyano‐Gilman reagents R2CuLi⋅LiCN (see diagram; formerly R2Cu(CN)Li2) are less than the well‐known effects of solvent (ether vs. THF) and TMSCl (in THF); this is consistent with the previous conclusion from several spectroscop...

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Published inChemistry : a European journal Vol. 5; no. 9; pp. 2680 - 2691
Main Authors Bertz, Steven H., Chopra, Anu, Eriksson, Magnus, Ogle, Craig A., Seagle, Paul
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 03.09.1999
WILEY‐VCH Verlag
Subjects
Aggregation
Alkylations
Cuprates
Lithium
Si ligands
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Summary:The differences in reactivity between iodo‐Gilman reagents R2CuLi⋅LiI and cyano‐Gilman reagents R2CuLi⋅LiCN (see diagram; formerly R2Cu(CN)Li2) are less than the well‐known effects of solvent (ether vs. THF) and TMSCl (in THF); this is consistent with the previous conclusion from several spectroscopic techniques and theoretical calculations that higher order cuprates are not involved.
Bibliography:ArticleID:CHEM2680
istex:44056CA091AE7031AB029A78AA65546095B5B558
ark:/67375/WNG-RVHV4PSH-J
ISSN:0947-6539
1521-3765
DOI:10.1002/(SICI)1521-3765(19990903)5:9<2680::AID-CHEM2680>3.0.CO;2-T