Methylenecyclopropane is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula (CH
2)
2CCH
2. It is a colourless easily condensed gas that is used as a
reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
in
organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
.
Synthesis
Methylenecyclopropane can be synthesised via an intramolecular cyclisation reaction from
methallyl chloride
Methallyl chloride is the organic compound with the formula CH2=C(CH3)CH2Cl. It is a colorless liquid and a lacrymator. Its properties are similar to those of allyl chloride. It is a strong alkylating agent used to install isobutenyl groups.
...
by treatment with a strong base such as
sodium amide
Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the formula . It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is whit ...
.
:
Reactions
Being a strained and unsaturated molecule methylenecyclopropane undergoes many reactions, especially in the presence of metal catalysts.
For example, methylenecyclopropanes can be converted to
cyclobutene
Cyclobutene is a cycloalkene. It is of interest in research but currently has no practical applications. It is a colorless easily condensed gas. A modern synthesis involves the 2-step dehydration of cyclobutanol. The compound was first prepared ...
s in the presence of a Platinum catalyst.
[''PtCl2-Catalyzed Rearrangement of Methylenecyclopropanes'' Alois Fürstner and Christophe Aïssa ]J. Am. Chem. Soc.
The ''Journal of the American Chemical Society'' is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society. The journal has absorbed two other publications in its history, the ''Journal of Analytic ...
; 2006; 128(19) pp 6306 -6307
Abstract
/ref> This can be considered similar to the ring expansion seen in vinylcyclopropane rearrangements
:
Substituted methylenecyclopropanes can also be involved in trimethylenemethane cycloaddition reactions.
See also
* Methylenecyclopropene
* 1-Methylcyclopropene
* Methylcyclopropane
Methylcyclopropane is an organic compound with the structural formula C3H5CH3. This colorless gas is the monomethyl derivative of cyclopropane
Cyclopropane is the cycloalkane with the molecular formula (CH2)3, consisting of three methylene gr ...
* Cyclopropene
Cyclopropene is an organic compound with the formula . It is the simplest cycloalkene. Because the ring is highly strained, cyclopropene is difficult to prepare and highly reactive. This colorless gas has been the subject for many fundamental st ...
References
Cyclopropanes
Vinylidene compounds