1,1-Bis(chloromethyl)ethylene
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1,1-Bis(chloromethyl)ethylene is the
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula CH2=C(CH2Cl)2. It is a colorless liquid. Featuring two allylic chloride substituents, it is di
alkylating agent Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...
.


Synthesis and reactions

It is prepared from
pentaerythritol Pentaerythritol is an organic compound with the formula C(CH2OH)4. The molecular structure can be described as a neopentane with one hydrogen atom in each methyl group replaced by a hydroxyl (–OH) group. It is therefore a polyol, specifically a ...
via a multistep procedure, beginning with the partial chlorination. The compound reacts with
diiron nonacarbonyl Diiron nonacarbonyl is an organometallic compound with the formula Fe2(CO)9. This metal carbonyl is a reagent in organometallic chemistry and of occasional use in organic synthesis. It is a more reactive source of Fe(0) than Fe(CO)5. This mica ...
to give the complex of
trimethylenemethane Trimethylenemethane (often abbreviated TMM) is a chemical compound with molecular formula, formula . It is a Charge (chemistry), neutral free molecule with two unsatisfied valence bonds, and is therefore a highly reactive free radical. Formally, ...
Fe(η4-C(CH2)3)(CO)3. It is also a precursor to .1.1
propellane In organic chemistry, propellane is any member of a class of polycyclic compound, polycyclic hydrocarbons, whose carbon skeleton consists of three rings of carbon atoms sharing a common carbon–carbon bond, carbon–carbon covalent bond. The co ...
.


References

{{DEFAULTSORT:Bis(chloromethyl)ethylene, 1,1- Chloroalkenes Vinylidene compounds