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Chapter 4

Chapter 4. Equilibrium of the compositions of Grignard reagents. n-butyllithium and potassium t-butoxide(super base). Retention of configuration. greater stability of sp 2 carbanions. Metal-halogen exchange. Metal-halogen exchange. Reduction of sulfides. dimethylaminonaphthalene(LDMAN).

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Chapter 4

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  1. Chapter 4

  2. Equilibrium of the compositions of Grignard reagents

  3. n-butyllithium and potassium t-butoxide(super base) Retention of configuration greater stability of sp2 carbanions

  4. Metal-halogen exchange

  5. Metal-halogen exchange

  6. Reduction of sulfides dimethylaminonaphthalene(LDMAN)

  7. Shapiro reaction vinyllithium compounds Nicolaou et al. J.Am.Chem.Soc.Vol.117,No.2,1995,634.

  8. Reactions with Alkylating Agents Limited in scope Radicals involved Hydrogen abstraction

  9. Allyllithium and benzyllithium reagents

  10. Ring closure Grignard reagents Reaction with Carbonyl Compoundds addition of Grignard reagents

  11. good leaving group +

  12. Competing reactions Meerwein- Pondorff-Verley reduction Enolization of the ketone

  13. homoallylic system 3 1 2 3 4 2 1 3 4 2 1 4

  14. Lewis acid

  15. directed ortho lithiation

  16. stable at low temperature

  17. (DMF)

  18. fast electron transfer step no free radicals are generated

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