Pentachlorocyclopropane is a chlorinated
cyclopropane
Cyclopropane is the cycloalkane with the molecular formula (CH2)3, consisting of three methylene groups (CH2) linked to each other to form a triangular ring. The small size of the ring creates substantial ring strain in the structure. Cyclopropane ...
with the chemical formula . It is a colourless liquid with a faint minty odour.
['' Pentachlorocyclopropane'' Stephen W. Tobey and Robert West The University of Wisconsin (1965)] It is thermally unstable above 100 °C; decomposition gives
1,1,3,3,3-pentachloropropene by
isomerisation
In chemistry, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautomeri ...
. Pentachlorocyclopropane can be obtained by the addition of
dichlorocarbene
Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapi ...
into
trichloroethylene
Trichloroethylene (TCE) is an organochloride with the formula C2HCl3, commonly used as an industrial metal-degreasing solvent. It is a clear, colourless, non-flammable, volatile liquid with a chloroform-like pleasant mild smell and sweet taste. in presence of a base. Pentachlorocyclopropane itself gives
tetrachlorocyclopropene
Tetrachlorocyclopropene is a chemical compound with the formula C3Cl4. A colorless liquid, the compound is a reagent used to prepare acetylene derivatives and in organic synthesis. It is prepared by addition of dichlorocarbene to trichloroethylen ...
when reacted with a base such as
potassium hydroxide
Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash.
Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which utili ...
by means of
dehydrohalogenation
In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate (chemistry), substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications.
Dehydrohalogen ...
.
[Advances in Alicyclic Chemistry. (2013). Elsevier Science. page 57]
References
Organochlorides
Cyclopropanes
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