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Bicyclobutane is an organic compound with … Bicyclobutane is an organic compound with the formula C4H6. It is a bicyclic molecule consisting of two cis-fused cyclopropane rings, and is a colorless and easily condensed gas. Bicyclobutane is noted for being one of the most strained compounds that is isolatable on a large scale — its strain energy is estimated at 63.9 kcal mol−1. It is a nonplanar molecule, with a dihedral angle between the two cyclopropane rings of 123°. The first reported bicyclobutane was the carboxyethyl derivative, C4H5CO2Et, which was prepared by dehydrohalogenation the corresponding bromocyclobutanecarboxylate ester with sodium hydride. The parent hydrocarbon was prepared from 1-bromo-3-chlorocyclobutane by conversion of the bromocyclobutanecarboxylate ester, followed by intramolecular Wurtz coupling using molten sodium. The intermediate 1-bromo-3-chlorocyclobutane can also be prepared via a modified Hunsdiecker reaction from 3-chlorocyclobutanecarboxylic acid using mercuric oxide and bromine: A synthetic approach to bicyclobutane derivatives involves ring closure of a suitably substituted 2-bromo-1-(chloromethyl)cyclopropane with magnesium in THF. Stereochemical evidence indicates that bicyclobutane undergoes thermolysis to form 1,3-butadiene with an activation energy of 41 kcal mol−1 via a concerted pericyclic mechanism (cycloelimination, [σ2s+σ2a]).c mechanism (cycloelimination, [σ2s+σ2a]).
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Bicyclo[1.1.0]butane
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Bicyclo[1.1.0]butane
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| rdfs:comment |
Bicyclobutane is an organic compound with … Bicyclobutane is an organic compound with the formula C4H6. It is a bicyclic molecule consisting of two cis-fused cyclopropane rings, and is a colorless and easily condensed gas. Bicyclobutane is noted for being one of the most strained compounds that is isolatable on a large scale — its strain energy is estimated at 63.9 kcal mol−1. It is a nonplanar molecule, with a dihedral angle between the two cyclopropane rings of 123°. A synthetic approach to bicyclobutane derivatives involves ring closure of a suitably substituted 2-bromo-1-(chloromethyl)cyclopropane with magnesium in THF.methyl)cyclopropane with magnesium in THF.
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Bicyclobutane
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