Cycloaddition
Cycloadditions form cyclic adducts without nucleophiles or electrophiles.
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A cycloaddition is a chemical reaction where two or more unsaturated molecules combine to form a cyclic adduct with reduced bond multiplicity.[1] A cyclization reaction results from this process.[1] Concerted, pericyclic pathways are characteristic of many cycloadditions, though some proceed through nonconcerted mechanisms.[1]
Quick Facts
- Field
- Organic chemistry
Facts from the source article.
Key facts and history
Two notation systems describe cycloadditions.[2] Thermal cycloadditions involve reactants in their ground electronic state and usually have (4n + 2) π electrons.[3] Woodward and Hoffmann introduced a square-bracket notation, preferred by IUPAC, that counts the electrons participating in the reaction rather than the atoms.[2] Light activation can also enable cycloadditions that involve 4n π electrons.[4]
What the research sources say
Sara M. Hein's 2006 paper in the Journal of Chemical Education describes an exploration of a photochemical pericyclic reaction using NMR data.[5]
References
- Wikipedia, "Cycloaddition" (CC BY-SA 4.0), which cites: "IUPAC Compendium of Chemical Terminology", IUPAC, 2009; "IUPAC Compendium of Chemical Terminology", IUPAC, 2009 (we also read that source) en.wikipedia.org
- Wikipedia, "Cycloaddition" (CC BY-SA 4.0), which cites: "IUPAC Compendium of Chemical Terminology", IUPAC, 2009 (we also read that source) en.wikipedia.org
- Wikipedia, "Cycloaddition" (CC BY-SA 4.0), which cites: Wang, X. and Houk, K.N., 1990. Carbenoid character in transition structures for reactions of ketenes with alkenes. Journal of the American Chemical Society, 112 (original not read by us) en.wikipedia.org
- Wikipedia, "Cycloaddition" (CC BY-SA 4.0), which cites: Hein, Sara M., "An Exploration of a Photochemical Pericyclic Reaction Using NMR Data", Journal of Chemical Education, June 2006, p. 940–942 (we also read that source) en.wikipedia.org
- Sara M. Hein, "An Exploration of a Photochemical Pericyclic Reaction Using NMR Data", Journal of Chemical Education (2006), doi:10.1021/ed083p940. OpenAlex metadata CC0; paper not read. doi.org
Each numbered sentence above was checked against the source it cites before publication. Sentences citing Wikipedia adapt text from the English Wikipedia article Cycloaddition (contributors), used under CC BY-SA 4.0; this entry is available under the same licence. Other sources were used for facts only; no text or images are copied from them.
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Sources
Compiled from Wikipedia and the sources listed below. Text from Wikipedia is available under CC BY-SA 4.0; this entry is adapted from it.
- Wikipedia: Cycloaddition (CC BY-SA 4.0).
- Word definitions: the , each quoted from its Wikipedia article.
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