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Bicyclobutane

Bicyclobutane
Bicyclobutane-2.svg
Identifiers
Properties
C4H6
Appearance colorless gas
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bicyclobutane is an organic compound with the formula C4H6. It is a bicyclic molecule consisting of two cis-fused cyclopropane rings, and is one of the most strained compounds isolatable on a large scale. It is a colorless easily condensed gas.

The first reported bicyclobutane was the carboxyethyl derivative, C4H5CO2Et, which was prepared by dehydrohalogenation the corresponding bromocyclobutanecarboxylate ester. The parent hydrocarbon was prepared by conversion of bromocyclobutanecarboxylate ester to 1-bromo-3-chlorocyclobutane, followed intramolecular Wurtz coupling using molten sodium:

It is a nonplanar molecule, with a dihedral angle of 123°.


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