1,3-Dipolar cycloaddition
A type of pericyclic chemical reaction / From Wikipedia, the free encyclopedia
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The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were described in the late 19th century to the early 20th century, following the discovery of 1,3-dipoles. Mechanistic investigation and synthetic application were established in the 1960s, primarily through the work of Rolf Huisgen.[1][2] Hence, the reaction is sometimes referred to as the Huisgen cycloaddition (this term is often used to specifically describe the 1,3-dipolar cycloaddition between an organic azide and an alkyne to generate 1,2,3-triazole). 1,3-dipolar cycloaddition is an important route to the regio- and stereoselective synthesis of five-membered heterocycles and their ring-opened acyclic derivatives. The dipolarophile is typically an alkene or alkyne, but can be other pi systems. When the dipolarophile is an alkyne, aromatic rings are generally produced.
Huisgen 1,3-dipolar cycloaddition | |
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Named after | Rolf Huisgen |
Reaction type | Ring forming reaction |
Identifiers | |
Organic Chemistry Portal | huisgen-1,3-dipolar-cycloaddition |
RSC ontology ID | RXNO:0000018 |