Bodroux–Chichibabin aldehyde synthesis
The Bodroux–Chichibabin aldehyde synthesis is a chemical reaction whereby a Grignard reagent is converted to an aldehyde one carbon longer.
Reaction of a Grignard reagent with triethyl orthoformate gives an acetal, which can be hydrolyzed to an aldehyde. For example, the synthesis of n-hexanal:[1]
See also
- Bouveault aldehyde synthesis
References
- ^ a b G. Bryant Bachman (1943). "n-Hexaldehyde". Organic Syntheses; Collected Volumes, vol. 2, p. 323.
- Bodroux, F. (1904). "Synthése d'aldehydes aromatiques" [Synthesis of aromatic aldehydes]. Compt. Rend. (in French). 138: 92.
- Tschitschibabin, A. E. (1904). "Eine neue allgemeine Darstellungsmethode der Aldehyde". Chemische Berichte (in German). 37: 186–188. doi:10.1002/cber.19040370133.
- Tschitschibabin, A. E. (1904). "Ueber den Hexahydro-m-toluylaldehyd". Chemische Berichte (in German). 37: 850–853. doi:10.1002/cber.190403701140.
- Smith, L. I.; Bayliss, M. (1941). "The Bodroux-Tschitschibabin, and the Bouveault Aldehyde Syntheses". J. Org. Chem. 6 (3): 437. doi:10.1021/jo01203a009.
- Smith, L. I.; Nichols, J. (1941). "The Synthesis of Aldehydes from Grignard Reagents. II. Polymethylbenzaldehydes". J. Org. Chem. 6 (4): 489. doi:10.1021/jo01204a003.
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Topics in organic reactions
- Addition reaction
- Elimination reaction
- Polymerization
- Reagents
- Rearrangement reaction
- Redox reaction
- Regioselectivity
- Stereoselectivity
- Stereospecificity
- Substitution reaction
- A value
- Alpha effect
- Annulene
- Anomeric effect
- Antiaromaticity
- Aromatic ring current
- Aromaticity
- Baird's rule
- Baker–Nathan effect
- Baldwin's rules
- Bema Hapothle
- Beta-silicon effect
- Bicycloaromaticity
- Bredt's rule
- Bürgi–Dunitz angle
- Catalytic resonance theory
- Charge remote fragmentation
- Charge-transfer complex
- Clar's rule
- Conformational isomerism
- Conjugated system
- Conrotatory and disrotatory
- Curtin–Hammett principle
- Dynamic binding (chemistry)
- Edwards equation
- Effective molarity
- Electromeric effect
- Electron-rich
- Electron-withdrawing group
- Electronic effect
- Electrophile
- Evelyn effect
- Flippin–Lodge angle
- Free-energy relationship
- Grunwald–Winstein equation
- Hammett acidity function
- Hammett equation
- George S. Hammond
- Hammond's postulate
- Homoaromaticity
- Hückel's rule
- Hyperconjugation
- Inductive effect
- Kinetic isotope effect
- LFER solvent coefficients (data page)
- Marcus theory
- Markovnikov's rule
- Möbius aromaticity
- Möbius–Hückel concept
- More O'Ferrall–Jencks plot
- Negative hyperconjugation
- Neighbouring group participation
- 2-Norbornyl cation
- Nucleophile
- Kennedy J. P. Orton
- Passive binding
- Phosphaethynolate
- Polar effect
- Polyfluorene
- Ring strain
- Σ-aromaticity
- Spherical aromaticity
- Spiroaromaticity
- Steric effects
- Superaromaticity
- Swain–Lupton equation
- Taft equation
- Thorpe–Ingold effect
- Vinylogy
- Walsh diagram
- Woodward–Hoffmann rules
- Woodward's rules
- Y-aromaticity
- Yukawa–Tsuno equation
- Zaitsev's rule
- Σ-bishomoaromaticity