:DeMayo reaction
{{Short description|Chemical reaction}}
The DeMayo reaction is a photochemical reaction in which the enol of a 1,3-diketone reacts with an alkene (or another species with a C=C bond) and the resulting cyclobutane ring undergoes a retro-aldol reaction to yield a 1,5-diketone:{{Cite book|title=Name reactions : a collection of detailed mechanisms and synthetic applications|author=Li, Jie Jack|date = 30 January 2014|isbn=9783319039794|edition= Fifth|location=Cham|oclc=870309747}}
The net effect is to add the two carbon atoms in the C=C double bond between the two carbonyl groups of the diketone. It is thus useful in syntheses both as a relatively selective way to join two parts of a molecule and as a way to apply the more developed chemistry of 1,3-diketone synthesis to 1,5-diketones. The first part is a [2+2] cycloaddition. The ensuing retro-aldol cleavage is favored by the relative instability of the cyclobutane ring.
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| De Mayo startAnimGif |
| An animation of the reaction mechanism |
