Organometallic Chemistry

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This is Prof. Hans Reich's collection of various topics on Organometallic Chemistry. Most of this content originated from his Chem 842 Course at the University of Wisconsin - Madison. Please choose a specific topic on the side menu for more detailed info.

Below is a general outline:

  • Organometallic Chemistry - Introduction
  • Organolithium Chemistry
    • Methods for preparing organolithium reagents
      • Li/H exchange, C-H acidities, kinetic and thermodynamic control, chelation
      • Reduction of halides (Cl, Br, I) and sulfides (PhS) using Li or Li+ArH-
      • Li/M exchange (M = Br, I, Sn, Hg, Se, Te)
      • Shapiro reaction - tosylhydrazones and lithium reagents
      • Addition of RLi to multiple bonds (C=O, C=C, CC)
    • Structure and dynamics in solid and solution
      • Aggregation - reactivity effects of donors
      • structural effect on reactivity - delocalization, ion pair structure
      • Stereochemistry of organolithium reagents
    • Synthetic applications of organolithium reagents
  • Organocopper and Organozinc Chemistry
    • Organocopper Chemistry
    • Organozinc Chemistry
    • Asymmetric synthesis using Zn and Cu reagents
  • Organotin and Organosilicon Chemistry
    • Comparison of C, Si, Ge and Sn
    • Preparation of organosilicon compounds and reagents
    • Electrophilic and nucleophilic cleavage of C-Si bonds (Peterson, Brook)
    • Preparation and uses of tin reagents (R3SnH, R3SnLi, R3SnSnR3, etc)
    • Formation of C-Sn bonds
    • Electrophilic, nucleophilic and radical substitution of C-Sn bonds, stereochemistry
  • Organoboron, Organoaluminum
    • Preparation of organoboranes
    • Typical reactions of organoboranes
    • Organoaluminum chemistry
    • Organoindium chemistry
  • Organosulfur and Organoselenium Chemistry
    • Comparison of S/Se/Te
    • Selenium reagents (PhSeX, PhSeSePh, PhSeM, etc)
    • Selenoxide elimination
    • Selenium electrophiles
    • -Lithio sulfides and selenides
  • Phosphorus, Arsenic, Antimony, Bismuth
    • General features
    • The Wittig, Horner and related reactions
  • The Halogens, and Others