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Homologation reaction

A homologation reaction, also known as homologization, is any chemical reaction that effects an overall increase of the carbon skeleton of a saturated reactant molecule.[1] The reactants undergo a homologation converting them into the next member of the homologous series. For example the reaction of aldehydes and ketones with diazomethane or methoxymethylenetriphenylphosphine effectively inserts a methylene (-CH2-) unit in the hydrocarbon chain and the reaction product is the next homologue.

Examples of homologation reactions include:

Some reactions increase the chain length by more than one unit. For example, the following are considered two-carbon homologation reactions:

  • Nucleophilic addition to ethylene oxide, resulting in a ring-opening and producing a primary alcohol with two extra carbons.
  • Malonic ester synthesis, which produces a carboxylic acid with two extra carbons.

See also


  1. ^ Encyclopedia of Inorganic Chemistry doi:10.1002/0470862106.id396
  2. ^ D. Gray, C. Concellon and T. Gallagher (2004). "Kowalski Ester Homologation. Application to the Synthesis of β-Amino Esters". J. Org. Chem. 69 (14): 4849-4851. doi:10.1021/jo049562h.
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Homologation_reaction". A list of authors is available in Wikipedia.
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