Tetramethylethylene is a
hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
with the formula Me
2C=CMe
2 (Me =
methyl
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...
). A colorless liquid, it is the simplest tetrasubstituted
alkene
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins.
The Internationa ...
.
Synthesis
It can be prepared by base-catalyzed isomerization of
2,3-dimethyl-1-butene. Another route involves direct
dimerization
In chemistry, dimerization is the process of joining two identical or similar molecular entities by bonds. The resulting bonds can be either strong or weak. Many symmetrical chemical species are described as dimers, even when the monomer is u ...
of
propylene
Propylene, also known as propene, is an unsaturated organic compound with the chemical formula . It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like o ...
.
It can also be produced by photolysis of
tetramethylcyclobutane-1,3-dione.
Reactions
Tetramethylethylene forms
metal-alkene complexes with low-valent metals and reacts with
diborane
Diborane(6), commonly known as diborane, is the chemical compound with the formula . It is a highly toxic, colorless, and pyrophoric gas with a repulsively sweet odor. Given its simple formula, borane is a fundamental boron compound. It has att ...
to give the monoalkyborane known as
thexylborane
Thexylborane is a borane with the formula e2CHCMe2BH2sub>2 (Me = methyl). The name derives from "''t''-hexylborane" (although the group is not the standard ''tert''-hexyl group), and the formula is often abbreviated ThxBH2. A colorless liquid, ...
.
[{{cite book, doi=10.1002/9780470132593.ch22, title=Di-μ-Chloro-Bis(η4-1,5-Cyclooctadiene)-Dirhodium(I), series=Inorganic Syntheses, pages=88–90, year=1990, volume=28, last1=Giordano, first1=G., last2=Crabtree, first2=R. H., chapter=Di-μ-Chloro-Bis(η 4 -1,5-Cyclooctadiene)-Dirhodium(I) , isbn=9780471526193 ]
Oxidation gives
pinacol.
It is a precursor to the herbicide
fenpropathrin.
[
]
References
Alkenes