cyclopropanone
Sign in to saveCyclopropanone is an organic compound with molecular formula (CH2)2CO consisting of a cyclopropane carbon framework with a ketone functional group. The parent compound is labile, being highly sensitive toward even weak nucleophiles. Surrogates of cyclopropanone include the ketals.
Wikidata facts
- Mass
- 56.026215
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- chemical formula
- C₃H₄O
- canonical SMILES
- C1CC1=O
- Commons category
- Cyclopropanone
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6 sectionsContents
- Preparation
- Structure
- Derivatives
- Coprine
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Cyclopropanone is an organic compound with molecular formula (CH2)2CO consisting of a cyclopropane carbon framework with a ketone functional group. The parent compound is labile, being highly sensitive toward even weak nucleophiles. Surrogates of cyclopropanone include the ketals.
==Preparation== Cyclopropanone has been prepared by reaction of ketene with diazomethane in an unreactive solvent such as dichloromethane. These solutions are stable at −78 °C. In the presence of protic reagents such as carboxylic acids, primary and secondary amines, and alcohols, cyclopropanone converts to adducts, which are often isolatable at room temperature: (CH2)2CO + X-H → (CH2)2C(X)(OH) (X-H = R2N-H, HO-H, RO-H) This reaction underlies cyclopropanone's polymerization at room temperature, initiated by traces of water. The isocyanate adducts can also be prepared directly through photochemical rearrangement of succinimino ethers.