Rapid-Injection NMR Study of Iodo- and Cyano-Gilman Reagents with 2-Cyclohexenone: Observation of π-Complexes and Their Rates of Formation
Journal of the American Chemical Society2002Vol. 124(46), pp. 13650–13651
Citations Over TimeTop 10% of 2002 papers
Steven H. Bertz, Clifford M. Carlin, Daniel A. Deadwyler, Michael D. Murphy, Craig A. Ogle, Paul Seagle
Abstract
Rapid-injection is a very useful technique for the preparation of temperature-sensitive and air-sensitive compounds in the cold, nitrogen-filled probe of an NMR spectrometer. We have used this method to prepare solutions of pi-complexes from 2-cyclohexenone and prototypical cuprates Me2CuLi.LiI and Me2CuLi.LiCN, and we have assigned structures on the basis of 1H and 13C NMR. In each case two pi-complexes were observed, and in the former, their rates of formation were measured by rapid-injection 1H NMR and EXSY spectroscopy. These results provide insights into the normal and anomalous conjugate addition reactions of organocuprates.
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