Subtle factors are important: radical formation and transmetallation in reactions of butyl cuprates with cyclohexyl iodide
- 10 January 2005
- journal article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 3 (3) , 392-394
- https://doi.org/10.1039/b416612d
Abstract
The reactions of Bu2CuLi·LiI and Bu2CuLi·LiCN with cyclohexyl iodide are critically dependent upon subtle factors such as the surface properties of the reaction vessel, nature of the solvent still and lot of ‘ultrapure’ copper salt in addition to major effects such as the Li counterion.Keywords
This publication has 21 references indexed in Scilit:
- Re-evaluation of Organocuprate Reactivity: Logarithmic Reactivity Profiles for Iodo- versus Cyano-Gilman Reagents in the Reactions of Organocuprates with 2-Cyclohexenone and IodocyclohexaneChemistry – A European Journal, 1999
- New Results Regarding the Structure and Reactivity of Cyanocuprates—The End of an Old ControversyAngewandte Chemie International Edition in English, 1999
- Deposition of thin conducting films of CuI on glassSolar Energy Materials and Solar Cells, 1998
- The Crystal Structures of a Lower Order and a “Higher Order” Cyanocuprate: [tBuCu(CN)Li(OEt2)2]∞ and [tBuCutBu{Li(thf)(pmdeta)}2CN]Angewandte Chemie International Edition in English, 1998
- The Use of15N NMR Spectroscopy To Resolve the “Higher Order Cyanocuprate” Controversy:15N,6Li, and13C NMR Spectroscopic Investigations of CuCN-Derived Butyl CupratesAngewandte Chemie International Edition in English, 1998
- New copper chemistry. 18. Reaction of Bu2CuLi.cntdot.LiI with alkyl iodides: evidence for free radicals and electron transferJournal of the American Chemical Society, 1991
- New copper chemistry. 10. Oxidation of organocuprates with nitroarenes: higher order cyanocuprates are differentJournal of the American Chemical Society, 1986
- Chemistry of higher order, mixed organocuprates. 4. The stereochemical outcome of substitution reactions at unactivated secondary centers using organocopper reagentsJournal of the American Chemical Society, 1982
- Radical reactions in liquid cyclohexane. I. The photolysis of solutions of diphenylmercury in cyclohexaneThe Journal of Physical Chemistry, 1967
- EVIDENCE FOR A TRACK EFFECT IN THE RADIOLYSIS OF LIQUID CYCLOHEXANEThe Journal of Physical Chemistry, 1963