Vinylsilane

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Vinylsilane
Vinylsilane.svg
Names
Preferred IUPAC name
Ethenylsilane
Other names
Vinyl silane
Identifiers
ECHA InfoCard 100.027.926 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
Properties
C2H6Si
Molar mass 58.155 g·mol−1
Appearancecolorless gas
Boiling point −22.8 °C (−9.0 °F; 250.3 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vinylsilane refers to an organosilicon compound with chemical formula CH2=CHSiH3. It is a derivative of silane (SiH4). The compound, which is a colorless gas, is mainly of theoretical interest. [1]

Contents

Substituted vinylsilanes

More commonly used than the parent vinylsilane are vinyl-substituted silanes with other substituents on silicon. In the area of organic synthesis, vinylsilanes are useful intermediates. [2]

Vinyltriethoxysilane is a common vinylsilane. Vinyltriethoxysilane.png
Vinyltriethoxysilane is a common vinylsilane.

In the area of polymer chemistry and materials science, vinyltrimethoxysilane or vinyltriethoxysilane serve as monomers and coupling agents.

Preparation

Vinylsilanes are often prepared by hydrosilylation of alkynes. They can be made by the reaction of alkenyl lithium and Grignard reagents with chlorosilanes. In some cases dehydrogenative silylation is another method. [3]

Related Research Articles

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An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties react to form a β-hydroxyaldehyde or β-hydroxyketone, and this is then followed by dehydration to give a conjugated enone.

The Heck reaction is the chemical reaction of an unsaturated halide with an alkene in the presence of a base and a palladium catalyst to form a substituted alkene. It is named after Tsutomu Mizoroki and Richard F. Heck. Heck was awarded the 2010 Nobel Prize in Chemistry, which he shared with Ei-ichi Negishi and Akira Suzuki, for the discovery and development of this reaction. This reaction was the first example of a carbon-carbon bond-forming reaction that followed a Pd(0)/Pd(II) catalytic cycle, the same catalytic cycle that is seen in other Pd(0)-catalyzed cross-coupling reactions. The Heck reaction is a way to substitute alkenes.

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The Ferrier rearrangement is an organic reaction that involves a nucleophilic substitution reaction combined with an allylic shift in a glycal. It was discovered by the carbohydrate chemist Robert J. Ferrier.

<span class="mw-page-title-main">Trimethylsilyl group</span> Functional group

A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom [−Si(CH3)3], which is in turn bonded to the rest of a molecule. This structural group is characterized by chemical inertness and a large molecular volume, which makes it useful in a number of applications.

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<span class="mw-page-title-main">Organosilicon chemistry</span> Organometallic compound containing carbon–silicon bonds

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<span class="mw-page-title-main">Richard F. Heck</span> American chemist (1931–2015)

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Reductions with hydrosilanes are methods used for hydrogenations and hydrogenolysis of organic compounds. The approach is a subset of Ionic hydrogenations. In this particular method, the substrate is treated with a hydrosilane and auxiliary reagent, often a strong acid, resulting in formal transfer of hydride from silicon to carbon. This style of reduction with hydrosilanes enjoys diverse if specialized applications.

<span class="mw-page-title-main">Anthracene-9-carbaldehyde</span> Chemical compound

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In organic chemistry, the Lombardo methylenation is a name reaction that allows for the methylenation of carbonyl compounds with the use of Lombardo's reagent, which is a mix of zinc, dibromomethane, and titanium tetrachloride.

References

  1. Ring, M. A.; O'Neal, H. E.; Rickborn, S. F.; Sawrey, B. A. (1983). "Kinetics of the high-temperature thermal decomposition of silanes and alkylsilanes". Organometallics. 2 (12): 1891–4. doi:10.1021/om50006a038.
  2. Fleming, Ian; Dunogues, Jacques; Smithers, Roger (1989). "The electrophilic substitution of allylsilanes and vinylsilanes". Organic Reactions. 37: 57–575. doi:10.1002/0471264180.or037.02. ISBN   0471264180.
  3. Lu, B.; Falck, J. R. (2010). "Iridium-Catalyzed (Z)-Trialkylsilylation of Terminal Olefins". J. Org. Chem. 75 (5): 1701–1705. doi:10.1021/jo902678p. PMC   2830331 . PMID   20136153.