# Vinyl halide

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{{Short description|Class of chemical compounds}}
[[Image:vinyl halide.png|thumb|right|100px|General structure of a vinyl halide, where X is a halogen and R is a [variable group.](/source/side_chain)]]
In [organic chemistry](/source/organic_chemistry), a '''vinyl halide''' is a compound with the formula CH<sub>2</sub>=CHX (X = [halide](/source/halide)). The term [vinyl](/source/vinyl_group) is often used to describe any alkenyl group. For this reason, alkenyl halides with the formula RCH=CHX are sometimes called vinyl halides. From the perspective of applications, the dominant member of this class of compounds is [vinyl chloride](/source/vinyl_chloride), which is produced on the scale of millions of tons per year as a precursor to [polyvinyl chloride](/source/polyvinyl_chloride).<ref name=Ullmann>{{cite book | author = E.-L. Dreher | author2 = T. R. Torkelson | author3 = K. K. Beutel | chapter = Chlorethanes and Chloroethylenes | title = Ullmann's Encyclopedia of Industrial Chemistry | year = 2011 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.o06_o01| isbn = 978-3527306732 }}</ref> [Polyvinyl fluoride](/source/Polyvinyl_fluoride) is another commercial product. Related compounds include [vinylidene chloride](/source/1%2C1-Dichloroethene) and [vinylidene fluoride](/source/vinylidene_fluoride).

==Synthesis==
{{See also|Vinyl iodide functional group}}

Vinyl chloride is produced by dehydrochlorination of 1,2-dichloroethane.<ref name=Ullmann/>

Due to their high utility, many approaches to vinyl halides have been developed, such as:

* reactions of vinyl [organometallic](/source/organometallic) species with halogens
400px|Carbometalation

* [Takai olefination](/source/Takai_olefination)
600px|Takai Olefination

* Stork-Zhao olefination with, e.g., [(Chloromethylene)triphenylphosphorane](/source/(Chloromethylene)triphenylphosphorane) - a modification of the [Wittig reaction](/source/Wittig_reaction)
Stork-Zhao Olefination

* [Olefin metathesis](/source/Olefin_metathesis)<ref>{{Cite journal|last1 = Koh|first1 = Ming Joo|last2 = Nguyen|first2 = Thach T.|last3 = Zhang|first3 = Hanmo|last4 = Schrock|first4 = Richard R.|last5 = Hoveyda|first5 = Amir H.|title = Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis|journal = Nature|volume = 531|issue = 7595|pages = 459–465|doi = 10.1038/nature17396|pmid=27008965|pmc=4858352|bibcode = 2016Natur.531..459K|year = 2016}}</ref><ref>{{Cite journal|last1=Nguyen|first1=Thach T.|last2=Koh|first2=Ming Joo|last3=Shen|first3=Xiao|last4=Romiti|first4=Filippo|last5=Schrock|first5=Richard R.|last6=Hoveyda|first6=Amir H.|date=2016-04-29|title=Kinetically controlled E-selective catalytic olefin metathesis|journal=Science|language=en|volume=352|issue=6285|pages=569–575|doi=10.1126/science.aaf4622|pmid=27126041|bibcode=2016Sci...352..569N|pmc=5748243}}</ref>

==Reactions==
Vinyl bromide and related alkenyl halides form the [Grignard reagent](/source/Grignard_reaction) and related [organolithium reagent](/source/organolithium_reagent)s. Alkenyl halides undergo base elimination to give the corresponding [alkyne](/source/alkyne).  Most important is their use in [cross-coupling reaction](/source/cross-coupling_reaction)s (e.g. [Suzuki-Miyaura coupling](/source/Suzuki_reaction), [Stille coupling](/source/Stille_reaction), [Heck coupling](/source/Heck_reaction), etc.).

==See also==
* [Vinyl iodide functional group](/source/Vinyl_iodide_functional_group)

==References==
{{Reflist}}

{{Organohalide-stub}}
Category:Organohalides

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Adapted from the Wikipedia article [Vinyl halide](https://en.wikipedia.org/wiki/Vinyl_halide) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Vinyl_halide?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.