Talk:Homologation reaction

Integration of homologization definition

I think that the Encyclopedia of Inorganic Chemistry definition and the definition that was given for "homologization" should be reconciled. Clearly the term is most often applied to the lengthening of carbon chains by adding methylene units, but it is also applied when the number of other repeat units is increased, such as in the Kiliani-Fischer synthesis.

Homologization is any chemical process converting one member of a homologues series to the next. For example the reaction of aldehydes and ketones with diazomethane or methoxymethylenetriphenylphosphine effectively inserts a methylene unit in the hydrocarbon chain and the reaction product is the next homologue. Chain homologization in sugars occurs in the Kiliani-Fischer synthesis.

Any suggestions for wording? M stone 16:57, 4 July 2007 (UTC)

I think homologization is a relatively uncommon variant of homologation. Google books gives only 15 results for homologization carbon, while it gives 562 for homologation carbon (the latter gives some false positives, but the conclusion doesn't change). --Itub 07:49, 9 July 2007 (UTC)

Seyferth-Gilbert

I split the original line into two:

• the Seyferth-Gilbert homologation
• the displacement of a halide by a cyanide group, which can be reduced to an amine.

This is because I read the S-G article and it didn't seem to imply a link with the latter. --Rifleman 82 03:13, 7 July 2007 (UTC)

Not really Homologations

The definition of homologation is historically quite clear and corresponds to the meaning of going from a lower to a higher member in a homologous series, compare also: http://en.wiktionary.org/wiki/homologation

The so-called "Seyferth-Gilbert homologation" is no homologation at all, and has not been called a homologation by the original authors, who certainly knew what a homologation was. (See the S-G article for the original literature references). Neither is the Kolbe nitrile synthesis a homologation in itself; it can be used for homologation via a sequence of, e.g., alcohol - alkyl halide - alkyl cyanide - homoalkyl amine - homo-alcohol (by diazotation). However, halides and amines are obviously not homologs. Citing the "Encyclopedia of Inorganic Chemistry" for a very organic thing is funny, in a way. In any case: the definition given now in the article "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." is certainly useless, as this would exclude unsaturated substrates and include all C-C bond forming reactions as homologations. No need for that. 134.130.101.232 (talk) 19:48, 19 June 2009 (UTC)

I would have to agree with your comments that the definition is not precise enough. I also think that the "chain reduction" section seems very out of place on this page (sorry V8rik). It is very nice content, but it over shadows the actual homologations. I wish there was a page devoted specifically to controlled degradations or chain length reductions or "inverse homologations" if such a term actually existed. M stone (talk) 01:47, 20 June 2009 (UTC)

Let's create an article on degradation reactions! --Itub (talk) 15:03, 20 June 2009 (UTC)

• In the Seyferth-Gilbert homologation the alkyne is converted to the next aldehyde by simple hydrolysis. V8rik (talk) 18:30, 20 June 2009 (UTC)

I have restored the Seyferth-Gilbert homologation. I would also agree with Itub that a degradation reaction page is a great idea. I am surprised that such a page and category don't already exist. I am having trouble finding a formal definition to start the page. M stone (talk) 03:45, 21 June 2009 (UTC)