title: Rapid-injection NMR study of iodo- and cyano-Gilman reagents with 2-cyclohexenone: observation of pi-complexes and their rates of formation.
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.
authors.affiliation: Department of Chemistry, University of North Carolina-Charlotte, UNCC Station, Charlotte, North Carolina 28223, USA. cogle@email.uncc.edu
authors.forename: Steven H
authors.initials: SH
authors.lastname: Bertz
authors.forename: Clifford M
authors.initials: CM
authors.lastname: Carlin
authors.forename: Daniel A
authors.initials: DA
authors.lastname: Deadwyler
authors.forename: Michael D
authors.initials: MD
authors.lastname: Murphy
authors.forename: Craig A
authors.initials: CA
authors.lastname: Ogle
authors.forename: Paul H
authors.initials: PH
authors.lastname: Seagle