Chemical reaction in which a ring is formed/broken by adding/removing a single atom
Example cheletropic reactions: Case 1: the single atom is the carbonyl carbon (C=O) that ends up in carbon monoxide (C≡O). Case 2: the single atom is the nitrogen atom in the diazenyl group (N=N), which ends up as dinitrogen (N≡N). The above are known as cheletropic eliminations because a small, stable molecule is given off in the reaction.[1] Case 3 & 4: the single atom is the sulfur in sulfur dioxide (SO2), which joins the alkene chains to form a ring.
In organic chemistry, cheletropic reactions, also known as chelotropic reactions,[2] are a type of pericyclic reaction (a chemical reaction that involves a transition state with a cyclic array of atoms and an associated cyclic array of interacting orbitals).[1] Specifically, cheletropic reactions are a subclass of cycloadditions. The key distinguishing feature of cheletropic reactions is that on one of the reagents, both new bonds are being made to the same atom.[3]
^ abEric V. Anslyn and Dennis A. Dougherty Modern Physical Organic Chemistry University Science Books, 2006.
^Chelotropic reaction IUPAC GoldBook
^Ian Fleming. Frontier Orbitals and Organic Chemistry Reactions. Wiley, 1976.
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organic chemistry, cheletropicreactions, also known as chelotropic reactions, are a type of pericyclic reaction (a chemical reaction that involves a transition...
and cheletropicreactions are often classed as group transfer reactions and cycloadditions/cycloeliminations, respectively, while dyotropic reactions and...
(3+2)cycloaddition. Cheletropicreactions are a subclass of cycloadditions. The key distinguishing feature of cheletropicreactions is that on one of the...
was to first allow butadiene to react with sulfur dioxide via a cheletropicreaction to give sulfolene. This was then hydrogenated using Raney nickel...
dioxide can react with certain 1,3-dienes in a cheletropicreaction to form cyclic sulfones. This reaction is exploited on an industrial scale for the synthesis...
species, such as carbenes, ylids and carbanions. Many of the reactions proceed in a cheletropic manner. Several methods exist for converting alkenes to cyclopropane...
The McCormack reaction is a method for the synthesis of organophosphorus compounds. In this reaction, a 1,3-diene and a source of R2P+ are combined to...
electrophiles, nucleophiles, or ambiphiles. Their reactions are typically concerted and often cheletropic.[citation needed] Singlet carbenes are typically...
bromination, followed by addition of the fourth t-Bu group. Photochemical cheletropic elimination of carbon monoxide of the cyclopentadienone gives the target...
cycloaddition reaction with Z-alkenes. The addition of (CH(SiMe3)2)2Sn, to 2,7-diphenylocta-2,3,5,6-tetraene proceeds in a cheletropic fashion, as allowed...
containing a ketone undergo a cheletropic extrusion reaction, leaving new carbon–carbon π bonds on the remaining structure. This reaction can be spontaneous, as...
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