Structure and Reactivity of Organolithium Reagents
   1. Structure and Reactivity of Organolithium Reagents
   2. Why Study Organolithium Reagents?
   3. Selectivity Effects in Organolithium Chemistry
   4. Some Organolithium Structural Types
   5. The Curtin-Hammett Principle
   6. Alkylation of Dithianes and Related Lithium Reagents
   7. Regioselectivity of Enone Additions
   8. The Curtin-Hammett Principle
   9. The Metal-Halogen Exchange - Interaction of Phenyllithium with Iodobenzene
  10. Apparatus
  11. RINMR Apparatus Picture
  12. RINMR Issues
  13. The Curtin Hammet Limitation: n-BuLi Dimer and Tetramer
  14. Sample RINMR Experiment
  15. A Rapid Injection NMR Study of BuLi Reaction with an Acetylene
  16. A Rapid Injection NMR Study of n-BuLi Reaction with an Acetylene
  17. Relative Reactivity of n-Butyllithium Dimer and Tetramer
  18. Relative Reactivity of n-BuLi Dimer and Tetramer
  19. Reactivity of Some Common Electrophiles with n-BuLi Dimer
  20. Amide vs. Ester Reactivity towards n-BuLi Dimer
  21. RINMR study of the n-BuLi-Dimer Reaction with Benzamide
  22. Study of a more Revealing System: p-Fluorophenyllithium
  23. Ester vs Amide Reactivity with p-Fluorophenyllithium
  24. RINMR Study of Benzamide Reaction with p-Fluorophenyllithium
  25. Aryllithium Reaction with Benzoate Ester: Interesting intermediate
  26. Direct Rate Comparison of Amide and Ester
  27. Reactivity of Mixed Organolithium Aggregates
  28. How is the Mixed Dimer Formed?
  29. Dimeric Enolate Comparable in Reactivity to Monomer?
  30. Effect of PMDTA on Reaction with Ester
  31. Reaction of Ketone with p-Fluorophenyllithium - does the Dimer React?
  32. Lithium Enolates
  33. NMR-Characterized Enolate Structures
  34. HMPA Titration of p-Fluoroacetophenone Lithium Enolate
  35. Carbon-13 Chemical Shifts of Aggregates
  36. LDA Mediated Enolization
of p-Fluoroacetophenone

  37. LDA Mediated Enolization of p-Fluoroacetophenone
  38. Ideal Rate Law of an Aldol Reaction with a Tetrameric Enolate
  39. Effect of 4-Substituted Benzaldehydes on Inital Rates
  40. Rate of Dissociation of Tetramer - Mixed Tetramer Formation
  41. Mechanistic Studies of the Aldol Reaction
  42. Tetrameric Enolate Aldol Reaction
  43. Dimer and Tetramer Enolate Reactivity: Aldol Reaction
  44. Dimer Enolate Reactivity: (CH3)3Si_I
  45. Conclusions - Dynamics of p-Fluoroacetophenone Enolate Formation and Reactions
  46. Summary
  47. Group Picture
  48. Acknowledgements
  49. Madison

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