1,6-Methano(10)annulene

1,6-Methano(10)annulene
Names

IUPAC name Bicyclo[4.4.1]undeca-1,3,5,7,9-pentaene
Identifiers
CAS Number	2443-46-1
3D model (Jmol)	Interactive image
ChemSpider	121264
PubChem	137603
InChI InChI=1S/C11H10/c1-2-6-11-8-4-3-7-10(5-1)9-11/h1-8H,9H2 Key: OORRQYZWSVJKSO-UHFFFAOYSA-N InChI=1/C11H10/c1-2-6-11-8-4-3-7-10(5-1)9-11/h1-8H,9H2 Key: OORRQYZWSVJKSO-UHFFFAOYAC
SMILES c1ccc2ccccc(c1)C2
Properties
Chemical formula	C₁₁H₁₂
Molar mass	144.22 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

1,6-Methano[10]annulene , 1,6-methanonaphthalene or homonaphthalene is a hydrocarbon with chemical formula C₁₁H₁₂.

It is analogous to cyclodecapentaene ([10]annulene), but with two hydrogen atoms replaced by a transannular methylene bridge (-CH
2-). This compound is aromatic as judged from lack in bond length alternation by x-ray crystallography and a telltale diamagnetic ring current from NMR spectroscopy.

Synthetic route to 1,6-methanoannulene

Its resonance energy is smaller than that of naphthalene.^[1]

References

↑ Roth, Wolfgang R.; Manfred Böhm (1983), "Resonance Energy of Bridged [10]Annulene", Angewandte Chemie International Edition in English, 22 (12): 1007–1008, doi:10.1002/anie.198310071

1,6-methano[10]annulene in Organic Syntheses, Coll. Vol. 6, p. 731; Vol. 54, p. 11 Online Article

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