LABORATORY FOR INSTRUMENTAL ORGANIC CHEMISTRY
Learning outcomes of the course unit
The intention of the course is to provide practical training in important aspects of structure determination by NMR. In the following monographic part, several aspects of the synthesis of C-C bonds through the use of organometallic compounds will be also briefly illustrated.
Chimica Organica I e II, Metodi Fisici in Chimica Organica
Course contents summary
Laboratory: Practical training for the set up of 1H and 13C experiments (optimizing parameters, pulse programs) on a spectrometer Bruker AC300 (300 MHz) and in processing and analyzing the NMR data.
Monographic part: brief classification of organometallic compounds. Synthesis of organolithium compounds. Reaction of organolithium and organomagnesium compounds. Coupling reactions for the preparation of C-C bond: RX+R’M=R-R’+MX. Catalytic cycle: oxidative addition, transmetallation, reductive elimination. Nature of the groups R and R’. Effect of the leaving group X. Sterical and electronic effects. Preparation of organozinc reagents and their reactions: Negishi coupling. Preparation of organotin reagents and their reactions: Stille coupling. Preparation of organoboron reagents and their reactions: Suzuki coupling. Sonogashira reaction. Homocoupling reactions. Heterocoupling reactions.
Monographic part: Rod Bates, Organic Synthesis using Transition Metals, Sheffield Academic Press, 2000. James, R. Hanson, Protecting groups in organic synthesis, Sheffield Academic Press, 2000. Clayden, Grreves, Warren, Wothers, Organic chemistry, Oxford university press, 2001