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Chemical compound From Wikipedia, the free encyclopedia
Cyclobutanone is an organic compound with molecular formula (CH2)3CO. It is a four-membered cyclic ketone (cycloalkanone). It is a colorless volatile liquid at room temperature. Since cyclopropanone is highly sensitive, cyclobutanone is the smallest easily handled cyclic ketone.
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Preferred IUPAC name
Cyclobutanone | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.013.405 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C4H6O | |
Molar mass | 70.091 g·mol−1 |
Appearance | Colorless liquid |
Density | 0.9547 g/cm3 (0 °C)[1] |
Melting point | −50.9 °C (−59.6 °F; 222.2 K)[1] |
Boiling point | 99.75 °C (211.55 °F; 372.90 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The Russian chemist Nikolai Kischner first prepared cyclobutanone in a low yield from cyclobutanecarboxylic acid.[2][3] Kischner's process, involving several steps, is cumbersome and inefficient; more efficient, high-yielding syntheses have since been developed.[4]
One strategy involves degradation of five-carbon building blocks. For example, the oxidative decarboxylation of cyclobutanecarboxylic acid was improved by the use of other reagents and methods.
A newer, more efficient preparation of cyclobutanone was found by P. Lipp and R. Köster in which a solution of diazomethane in diethyl ether is reacted with ketene.[5] This reaction is based on a ring expansion of the cyclopropanone intermediate initially formed, wherein molecular nitrogen is split off:
The reaction mechanism was confirmed by a reaction using 14C-labeled diazomethane.[6]
Another synthesis of cyclobutanone involves lithium iodide catalyzed rearrangement of oxaspiropentane, which is formed by epoxidation of the easily accessible methylenecyclopropane:[7][8]
Cyclobutanone can also be prepared in a two step procedure by dialkylation of 1,3-dithiane with 1-bromo-3-chloropropane followed by deprotection to the ketone with mercuric chloride (HgCl2) and cadmium carbonate (CdCO3).[9]
Cyclobutanones are the intermediates of the homo-Favorskii rearrangement, and can be isolated when nucleophiles are absent, as in the synthesis of kelsoene:
At about 350 °C, cyclobutanone decomposes into ethylene and ketene.[10] The activation energy for this [2+2] cycloelimination is 52 kcal/mol. The reverse reaction, the [2+2] cycloaddition of ketene and ethylene, has never been observed.
Other cyclic ketones:
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