Vinylidene group

Vinylidenes (examples) Vinylidene group marked in blue
Vinylidene chloride
Vinylidene fluoride
General formula

The vinylidene group is a functional group of the vinylidenes. It occurs, among other things, in monomers that are used to manufacture polymers .

IUPAC nomenclature

In the IUPAC nomenclature, 1,1-ethenediyl describes the connectivity R ¹ R ² > C = CH ₂ . The related species of ethenylidenes have the connectivity R = C = CH2.

Polymerization

An example is 1,1-dichloroethene , commonly referred to as vinylidene chloride. Vinylidene chloride and fluoride can be converted to linear polymers, polyvinylidene chloride (PVDC) and polyvinylidene fluoride (PVDF). The polymerization reaction is:

n CH ₂ = CX ₂ → (CH ₂ −CX ₂ ) _n

These vinylidene polymers are isomeric to those made from vinylene monomers. This is how polyvinylene fluoride is made from vinylene fluoride (HFC = CHF).

Itaconic acid dichloride reacts with diamines to form polyamides that contain a reactive vinylidene group.

Complex chemistry

Vinylidenes appear as ligands in organometallic chemistry. With vinylidene rhodium complexes, C − C bond linkages of a methyl group with a vinylidene group are possible.

Individual evidence

↑ Entry on vinylidenes . In: IUPAC Compendium of Chemical Terminology (the “Gold Book”) . doi : 10.1351 / goldbook.V06623 Version: 2.3.3.
↑ C. Wang, X. Wang, Z. Wie, X. Zeng: Synthesis and characterization of poly (p-phenyleneitaconamide) . In: Polym. Mater. Sci. Closely. tape 34 , no. 6 , 2018, p. 9–15 , doi : 10.16865 / j.cnki.1000-7555.2018.06.002 .
^ Barry M. Trost, Andrew McClory: Metal Vinylidenes as Catalytic Species in Organic Reactions . In: Chemistry - An Asian Journal . tape 3 , no. 2 , February 1, 2008, p. 164–194 , doi : 10.1002 / asia.200700247 .
↑ Helmut Werner, Justin Wolf, Gerhard Müller, Carl Krüger: Ambident behavior of mononuclear vinylidene rhodium complexes - a new type of CC linkage of a methyl group with a vinylidene group . In: Angewandte Chemie . tape 96 , no. 6 , 1984, pp. 421-422 , doi : 10.1002 / anie.19840960608 .

[1] Entry on vinylidenes . In: IUPAC Compendium of Chemical Terminology (the “Gold Book”) . doi : 10.1351 / goldbook.V06623 Version: 2.3.3.

[2] C. Wang, X. Wang, Z. Wie, X. Zeng: Synthesis and characterization of poly (p-phenyleneitaconamide) . In: Polym. Mater. Sci. Closely. tape 34 , no. 6 , 2018, p. 9–15 , doi : 10.16865 / j.cnki.1000-7555.2018.06.002 .

[3] Barry M. Trost, Andrew McClory: Metal Vinylidenes as Catalytic Species in Organic Reactions . In: Chemistry - An Asian Journal . tape 3 , no. 2 , February 1, 2008, p. 164–194 , doi : 10.1002 / asia.200700247 .

[4] Helmut Werner, Justin Wolf, Gerhard Müller, Carl Krüger: Ambident behavior of mononuclear vinylidene rhodium complexes - a new type of CC linkage of a methyl group with a vinylidene group . In: Angewandte Chemie . tape 96 , no. 6 , 1984, pp. 421-422 , doi : 10.1002 / anie.19840960608 .