Vinyl halide: Difference between revisions
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{{Short description|Class of chemical compounds}} |
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{{Refimprove|date=June 2016}} |
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[[Image:vinyl halide.png|thumb|right|100px|General structure of a vinyl halide, where X is a halogen and R is a [[side chain| |
[[Image:vinyl halide.png|thumb|right|100px|General structure of a vinyl halide, where X is a halogen and R is a [[side chain|variable group.]]]] |
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In [[organic chemistry]], a '''vinyl halide''' is a compound with the formula CH<sub>2</sub>=CHX (X = [[halide]]). The term [[vinyl group|vinyl]] 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]], which is produced on the scale of millions of tons per year as a precursor to [[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]] is another commercial product. Related compounds include [[1,1-Dichloroethene|vinylidene chloride]] and [[vinylidene fluoride]]. |
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In [[organic chemistry]], a '''vinyl halide''' is any [[alkene]] with at least one [[halide]] [[substituent]] bonded directly on one of the alkene carbons. [[Vinyl chloride]] is one such substance. |
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==Synthesis== |
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| ⚫ | Vinyl |
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{{See also|Vinyl iodide functional group}} |
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Vinyl chloride is produced by dehydrochlorination of 1,2-dichloroethane.<ref name=Ullmann/> |
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Due to their high utility, many approaches to vinyl halides have been developed, such as: |
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Besides, some vinyl halides are useful for synthesizing [[polymer]]s and [[copolymer]]s, see e.g. [[polyvinyl chloride]] or [[polyvinyl fluoride]]. The unsubstituted vinyl halides (R<sub>1</sub> = R<sub>2</sub> = R<sub>3</sub> = H) may polymerize spontaneously under certain conditions. |
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* reactions of vinyl [[organometallic]] species with halogens |
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[[File:Carbometalation.png|400px|Carbometalation]] |
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* [[Takai olefination]] |
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| ⚫ | <ref>{{Cite journal|last=Nguyen|first=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 |
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[[File:TakaiMechanism.svg|600px|Takai Olefination]] |
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* Stork-Zhao olefination with, e.g., [[(Chloromethylene)triphenylphosphorane]] - a modification of the [[Wittig reaction]] |
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{{DEFAULTSORT:Vinyl Halide}} |
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[[File:Stork-Zhao Olefination.jpg|Stork-Zhao Olefination]] |
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| ⚫ | * [[Olefin metathesis]]<ref>{{Cite journal|last = Koh|first = 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> |
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==Reactions== |
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| ⚫ | Vinyl bromide and related alkenyl halides form the [[Grignard reaction|Grignard reagent]] and related [[organolithium reagent]]s. Alkenyl halides undergo base elimination to give the corresponding [[alkyne]]. Most important is their use in [[cross-coupling reaction]]s (e.g. [[Suzuki reaction|Suzuki-Miyaura coupling]], [[Stille reaction|Stille coupling]], [[Heck reaction|Heck coupling]], etc.). |
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==See also== |
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* [[Vinyl iodide functional group]] |
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| ⚫ | <ref>{{Cite journal|last=Nguyen|first=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> |
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{{Organohalide-stub}} |
{{Organohalide-stub}} |
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Latest revision as of 01:38, 21 April 2024
In organic chemistry, a vinyl halide is a compound with the formula CH2=CHX (X = halide). The term vinyl 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, which is produced on the scale of millions of tons per year as a precursor to polyvinyl chloride.[1] Polyvinyl fluoride is another commercial product. Related compounds include vinylidene chloride and vinylidene fluoride.
Synthesis
[edit]Vinyl chloride is produced by dehydrochlorination of 1,2-dichloroethane.[1]
Due to their high utility, many approaches to vinyl halides have been developed, such as:
- reactions of vinyl organometallic species with halogens
- Stork-Zhao olefination with, e.g., (Chloromethylene)triphenylphosphorane - a modification of the Wittig reaction
Reactions
[edit]Vinyl bromide and related alkenyl halides form the Grignard reagent and related organolithium reagents. Alkenyl halides undergo base elimination to give the corresponding alkyne. Most important is their use in cross-coupling reactions (e.g. Suzuki-Miyaura coupling, Stille coupling, Heck coupling, etc.).
See also
[edit]References
[edit]- ^ a b E.-L. Dreher; T. R. Torkelson; K. K. Beutel (2011). "Chlorethanes and Chloroethylenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o06_o01. ISBN 978-3527306732.
- ^ Koh, Ming Joo; Nguyen, Thach T.; Zhang, Hanmo; Schrock, Richard R.; Hoveyda, Amir H. (2016). "Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis". Nature. 531 (7595): 459–465. Bibcode:2016Natur.531..459K. doi:10.1038/nature17396. PMC 4858352. PMID 27008965.
 | This article about an organic halide is a stub. You can help Wikipedia by expanding it. |
- ^ Nguyen, Thach T.; Koh, Ming Joo; Shen, Xiao; Romiti, Filippo; Schrock, Richard R.; Hoveyda, Amir H. (2016-04-29). "Kinetically controlled E-selective catalytic olefin metathesis". Science. 352 (6285): 569–575. Bibcode:2016Sci...352..569N. doi:10.1126/science.aaf4622. PMC 5748243. PMID 27126041.