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Advanced Organic Chemistry/ Organic Synthesis – CH 621 C-C ...
Transcript of Advanced Organic Chemistry/ Organic Synthesis – CH 621 C-C ...
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Advanced Organic Chemistry/ Organic Synthesis – CH 621
C-C Bond Formation through Carbanions
Bela TorokDepartment of Chemistry
University of Massachusetts BostonBoston, MA
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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
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C-C bond formation through carbanions
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C-C bond formation through carbanions
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C-C bond formation through carbanions
Knoevenagel condensation
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C-C bond formation through carbanions
Knoevenagel condensation
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C-C bond formation through carbanions
Doebner condensation
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C-C bond formation through carbanions
Moderate acidity: pKa
9-10 nitromethane
19-27 others Equilibrium concentration of the carbanion
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C-C bond formation through carbanions
Claisen estercondensation
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C-C bond formation through carbanions
Indirect method tounsaturated aldehydes
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C-C bond formation through carbanions
Georg WittigNobel Prize1979
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C-C bond formation through carbanions
Wilsmeier-Haack-Arnoldreaction
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C-C bond formation through carbanions
Wilsmeier-Haack-reaction
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C-C bond formation through carbanions
Reimer-Tiemannreaction
Kolbe-Schmittreaction
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C-C bond formation through carbanions
Mannichreaction
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C-C bond formation through carbanions
Mannichreaction
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Summary
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Summary
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Summary
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Summary