cycloaddition
Sign in to savethumb|261x261px|Non-ionic Cycloadditions In organic chemistry, a cycloaddition is a chemical reaction in which "two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity". The resulting reaction is a cyclization reaction. Many but not all cycloadditions are concerted and thus pericyclic. Nonconcerted cycloadditions are not pericyclic. As a class of addition reaction, cycloadditions permit carbon–carbon bond formation without the use of a nucleophile or electrophile.
Article
11 sectionsContents
- Thermal cycloadditions and their stereochemistry
- Photochemical cycloadditions and their stereochemistry
- Types of cycloaddition
- Diels-Alder reactions
- Huisgen cycloadditions
- Nitrone-olefin cycloaddition
- Cheletropic reactions
- Other
- Formal cycloadditions
- Iron-catalyzed [2+2] olefin cycloaddition
- References
thumb|261x261px|Non-ionic Cycloadditions In organic chemistry, a cycloaddition is a chemical reaction in which "two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity". The resulting reaction is a cyclization reaction. Many but not all cycloadditions are concerted and thus pericyclic. Nonconcerted cycloadditions are not pericyclic. As a class of addition reaction, cycloadditions permit carbon–carbon bond formation without the use of a nucleophile or electrophile.
Cycloadditions can be described using two systems of notation. An older but still common notation is based on the size of linear arrangements of atoms in the reactants. It uses parentheses: where the variables are the numbers of linear atoms in each reactant. The product is a cycle of size . In this system, the standard Diels-Alder reaction is a [4+2]-cycloaddition, the 1,3-dipolar cycloaddition is a [3+2]-cycloaddition and cyclopropanation of a carbene with an alkene a [2+1]-cycloaddition.