Advanced Organic Chemistry/ Organic Synthesis – CH 621
C-C Bond Formation through Carbanions
Bela TorokDepartment of Chemistry
University of Massachusetts BostonBoston, MA
C-C bond formation through carbanions
Stability of carbanions
- Carbanions stibilized by two –M groups
- Carbanions stabilized by one –M group
- Carbanions stabilized by P or S
- Nucleophilic acylations
- Alkene, arene, heteroarene nucleophiles
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
Knoevenagel condensation
C-C bond formation through carbanions
Knoevenagel condensation
C-C bond formation through carbanions
Doebner condensation
C-C bond formation through carbanions
C-C bond formation through carbanions
Moderate acidity: pKa
9-10 nitromethane
19-27 others Equilibrium concentration of the carbanion
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
Claisen estercondensation
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
Indirect method tounsaturated aldehydes
C-C bond formation through carbanions
C-C bond formation through carbanions
Georg WittigNobel Prize1979
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
C-C bond formation through carbanions
Wilsmeier-Haack-Arnoldreaction
C-C bond formation through carbanions
Wilsmeier-Haack-reaction
C-C bond formation through carbanions
Reimer-Tiemannreaction
Kolbe-Schmittreaction
C-C bond formation through carbanions
C-C bond formation through carbanions
Mannichreaction
C-C bond formation through carbanions
Mannichreaction
Summary
Summary
Summary
Summary
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