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Heteroelements (M2R CO7)

3CAEA2 Heteroelements (M2R CO7) Materials and Chemistry S9
Lessons : 20 h TD : 0 h TP : 0 h Project : 0 h Total : 20 h
Co-ordinator : Stephane Perrio
Prerequisite
Organic synthesis courses from previous levels.
Course Objectives
To acquire knowledge concerning the specific reactivity of phosphorus, sulphur, selenium and fluorinated reagents/reactants in organic synthesis.
To know the impact of the presence of the P, S, Se, F heteroatoms in terms of reactivity and selectivity.
Syllabus
General background concerning P, S, Se and F heteroatoms. More specifically for each one:
Phosphorus: Synthesis of phosphorus reagents. Nucleophilic reactivity (phosphonium, epoxide reduction, Arbusov, Michaelis Arbusov and Michaelis Becker, Mukayama, Corey Fuchs, Perkow). Electrophilic reactivity (ROH chlorination). Mitsunobu, Staudinger reactions. Phosphonium and ylides. Formation of C=C bonds (Wittig, Wittig-Horner, Horner, Wadsworth-Emmonds, Corey-Winter). Phosphorus compounds and organometallic catalysis/organocatalysis.
Sulphur and selenium: Synthesis of organosulfur and selenium reagents. Functional modification (introduction of a double bond, Pummerer, desulfurization, Barton-Mc Combie, addition, thioureas in organocatalysis) Sulfur intermediates (carbanions, C=S, Ramberg-Backlund, Julia olefination, ylides, pericyclic reactions).
Fluorine: Monofluorination (nucleophilic and electrophilic). Difluorination. Trifluoromethylation (radical, nucleophilic, electrophilic). Asymmetric synthesis.
Practical work (TD or TP)
Tutorial: use of the theoretical knowledge to solve synthesis problems and interpretation of the results through mechanisms. Previous final exams provided.
Acquired skills
Knowledge of the impact, in terms of reactivity and selectivity, of P, S, Se and F based compounds.
Bibliography
P. J. Murphy, Organophosphorus Reagents, Oxford University Press, 2004.
G. H. Whitham, «Organosulfur Chemistry», Oxford University Press, Oxford, 1995.
«Organoselenium Chemistry: Synthesis and Reactions», Wiley, Weinheim, 2012.

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