Cyclobutane

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Organic compound (CH2)4

title: "Cyclobutane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["cycloalkanes", "cyclobutanes"] description: "Organic compound (CH2)4" topic_path: "general/cycloalkanes" source: "https://en.wikipedia.org/wiki/Cyclobutane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Organic compound (CH2)4 ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 439048895 | Name = Cyclobutane | ImageFile = Siklobüten für Kurdi.svg | ImageClass = skin-invert-image | ImageSize = 100px | ImageFileL1 = Cyclobutane-buckled-3D-balls.png | ImageClassL1 = bg-transparent | ImageNameL1 = Cyclobutane | ImageFileR1 = Cyclobutane-buckled-3D-vdW.png | ImageClassR1 = bg-transparent | ImageNameR1 = Cyclobutane | PIN = Cyclobutane | OtherNames = Ethene dimer Biethylene Diethylene |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 287-23-0 | UNII_Ref = | UNII = 5X619RB2CY | SMILES = C1CCC1 | PubChem = 9250 | ChemSpiderID_Ref = | ChemSpiderID = 8894 | EC_number = 206-014-5 | UNNumber = 2601 | ChEBI = 30377 | Beilstein = 1900183 | Gmelin = 81684 | InChI = 1/C4H8/c1-2-4-3-1/h1-4H2 | InChIKey = PMPVIKIVABFJJI-UHFFFAOYAP | StdInChI_Ref = | StdInChI = 1S/C4H8/c1-2-4-3-1/h1-4H2 | StdInChIKey_Ref = | StdInChIKey = PMPVIKIVABFJJI-UHFFFAOYSA-N |Section2={{Chembox Properties | Formula = C4H8 | Appearance = Colorless gas | MolarMass = 56.107 g/mol | MeltingPtC = -91 | BoilingPtC = 12.5 | Density = 0.720 g/cm3 |Section7={{Chembox Hazards | GHSPictograms = | GHSSignalWord = Danger | HPhrases = | PPhrases = | NFPA-H=1 | NFPA-F=4 | NFPA-R=0 |Section8={{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = Butane | OtherFunction_label = alkane | OtherCompounds = Cyclobutene; Cyclobutadiene; Cyclopropane; Cyclopentane }}

Cyclobutane is a cycloalkane and organic compound with the formula (CH2)4. Cyclobutane is a colourless gas and is commercially available as a liquefied gas. Derivatives of cyclobutane are called cyclobutanes. Cyclobutane itself is of no commercial or biological significance, but more complex derivatives are important in biology and biotechnology.

Structure

The bond angles between carbon atoms are significantly strained and as such have lower bond energies than related linear or unstrained hydrocarbons, e.g. butane or cyclohexane. As such, cyclobutane is unstable above about 500 °C.

The four carbon atoms in cyclobutane are not coplanar; instead, the ring typically adopts a folded or "puckered" conformation. This implies that the C-C-C angle is less than 90°. One of the carbon atoms makes a 25° angle with the plane formed by the other three carbons. In this way, some of the eclipsing interactions are reduced. The conformation is also known as a "butterfly". Equivalent puckered conformations interconvert: :[[File:CyclobutaneConf2.png|330px]]

Cyclobutanes in biology and biotechnology

:[[File:Pentacycloanammoxic acid.svg|300px|Pentacycloanammoxic acid]] Despite the inherent strain, the cyclobutane motif is indeed found in nature. One example is pentacycloanammoxic acid,{{cite journal | author = J. S. Sinninghe Damsté, M. Strous, W. I. C. Rijpstra, E. C. Hopmans, J. A. J. Geenevasen, A. C. T. van Duin, L. A. van Niftrik and M. S. M. Jetten | year = 2002 | title = Linearly concatenated cyclobutane lipids form a dense bacterial membrane | journal = Nature | doi = 10.1038/nature01128 | pmid = 12384695 | bibcode = 2002Natur.419..708S | s2cid = 4373854 | volume = 419 | issue = 6908 | pages = 708–712 | last1=Mascitti |first1=Vincent | last2=Corey |first2=E. J. |authorlink2=E. J. Corey | year = 2006 | title = Enantioselective Synthesis of Pentacycloanammoxic Acid | journal = J. Am. Chem. Soc. | doi = 10.1021/ja058370g | pmid = 16522072 | volume = 128 | issue = 10 | pages = 3118–9

Cyclobutane photo dimers (CPD) are formed by photochemical reactions that result in the coupling of the C=C double bonds of pyrimidines.{{cite journal | last = Setlow |first = R. B. | year = 1966 | title = Cyclobutane-Type Pyrimidine Dimers in Polynucleotides | journal =Science | pmid = 5328566 | bibcode = 1966Sci...153..379S | s2cid = 11210761 | doi = 10.1126/science.153.3734.379 | volume = 153 | issue = 3734 | pages = 379–386 | author = Expert reviews in molecular medicine | date = 2 December 2002 | title = Structure of the major UV-induced photoproducts in DNA.

Carboplatin is a popular anticancer drug that is derived from cyclobutane-1,1-dicarboxylic acid.

Preparation

Many methods exist for the preparation of cyclobutanes. Alkenes dimerize upon irradiation with UV light, and, in the Norrish-Yang reaction, irradiated carbonyls cyclize to a cyclobutanol. Ketenes attack electron-rich alkenes to give cyclobutanones. 1,4-Dihalobutanes convert to cyclobutanes upon dehalogenation with reducing metals.

Cyclobutane was first synthesized in 1907 by James Bruce and Richard Willstätter by hydrogenating cyclobutene in the presence of nickel.

References

(2005). "The Chemistry of Cyclobutanes". John Wiley & Sons.
"Cyclobutane".
(1907). "Zur Kenntnis der Cyclobutanreihe". Berichte der Deutschen Chemischen Gesellschaft.

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