The conjoined cyclobutene rings of Dewar benzene form an obtuse angle.
Names
Preferred IUPAC name
Bicyclo[2.2.0]hexa-2,5-diene
Identifiers
CAS Number
5649-95-6Y
3D model (JSmol)
Interactive image
ChemSpider
89242Y
PubChem CID
98808
UNII
885QNL8RTBY
CompTox Dashboard (EPA)
DTXSID00205033
InChI
InChI=1S/C6H6/c1-2-6-4-3-5(1)6/h1-6HY
Key: CTLSARLLLBZBRV-UHFFFAOYSA-NY
InChI=1/C6H6/c1-2-6-4-3-5(1)6/h1-6H
Key: CTLSARLLLBZBRV-UHFFFAOYAO
SMILES
C\1=C\C2/C=C\C/12
Properties
Chemical formula
C6H6
Molar mass
78.1 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Dewar benzene (also spelled dewarbenzene) or bicyclo[2.2.0]hexa-2,5-diene is a bicyclic isomer of benzene with the molecular formula C6H6. The compound is named after James Dewar who included this structure in a list of possible C6H6 structures in 1869.[1] However, he did not propose it as the structure of benzene, and in fact he supported the correct structure previously proposed by August Kekulé in 1865.[2]
^Cite error: The named reference Dewar was invoked but never defined (see the help page).
^Cite error: The named reference Baker was invoked but never defined (see the help page).
Dewarbenzene (also spelled dewarbenzene) or bicyclo[2.2.0]hexa-2,5-diene is a bicyclic isomer of benzene with the molecular formula C6H6. The compound...
1867 Dewar described several chemical formulas for benzene, which were published in 1869. One of the formulae, which does not represent benzene correctly...
Cryogenic storage dewar, a specialised vacuum flask for extremely cold fluids Dewarbenzene, an isomer of benzene named for James DewarDewar's, makers of a...
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal...
can also be formed in low yield (along with fulvene and Dewarbenzene) by irradiation of benzene at 237 to 254 nm. The hydrocarbon in solution was described...
isomers of benzeneBenzeneDewarbenzene Prismane Benzvalene Bicyclopropenyl The valence isomers are not restricted to isomers of benzene. Valence isomers...
example, Ladenburg proposed prismane, Dewar proposed Dewarbenzene, and Koerner and Claus proposed Claus' benzene. Some of these structures would be synthesized...
involves an elimination reaction from a Dewarbenzene derivative. The structure itself can be envisioned as benzene with an internal bridge, and calculations...
cyclobutadiene reacts with electron-deficient alkynes to form a Dewarbenzene: The Dewarbenzene converts to dimethyl phthalate on heating at 90 °C. One cyclobutadiene...
formula C6(CH3)6. It is an aromatic compound and a derivative of benzene, where benzene's six hydrogen atoms have each been replaced by a methyl group. In...
now-obsolete route to Cp* complexes involves the use of hexamethyl Dewarbenzene. This method was traditionally used for preparation of the chloro-bridged...
compound containing one or more silicon atoms instead of carbon atoms in benzene. A single substitution gives silabenzene proper; additional substitutions...
[6]-cyclophane. This highly distorted cyclophane photochemically converts to the Dewarbenzene derivative. Heat reverses the reaction. With dimethyl acetylenedicarboxylate...
chloride. In presence of silver ions bicycloprop-2-enyl rearranges to Dewarbenzene. The compound can also be trapped by cyclopentadiene. Above -10 °C it...
biosynthesis of cholesterol. Van Tamelen was also the first to synthesise Dewarbenzene. He developed a system for nitrogen fixation using titanocene. van Tamelen...
UV light causes gaseous HFB to isomerize to hexafluoro derivative of Dewarbenzene. Hexafluorobenzene has been used as a reporter molecule to investigate...
He is remembered for his early investigations of the benzene structure known as the Dewarbenzene. In 1868 he introduced the term valenz (valence) into...
studied by its hexamethyl derivative. The synthesis starts at hexamethyl Dewarbenzene (compound I in table 4) reacting with Cl2 into 5,6-dichloro-1,2,3,4...
prepared by the reaction of hydrated iridium trichloride with hexamethyl Dewarbenzene. More conveniently, the compound is prepared by the reaction of hydrated...
(1869) and James Dewar (1871) suggested that, in analogy between quinoline and naphthalene, the structure of pyridine is derived from benzene by substituting...
idea of resonance between Friedrich August Kekulé von Stradonitz and James Dewar structures. In contrast, molecular orbital theory views aromaticity as delocalization...
more atoms. Some simple organic conjugated molecules are 1,3-butadiene, benzene, and allylic carbocations. The largest conjugated systems are found in...
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