Benzotriyne

Hypothetical molecule; 6-sided ring composed of pure carbon

Benzotriyne
Names

Preferred IUPAC name Hexadehydrobenzene
Identifiers
CAS Number	21894-87-1
3D model (JSmol)	Alternating form: Interactive image Cumulene form: Interactive image
PubChem CID	12334440
CompTox Dashboard (EPA)	DTXSID70491042
InChI InChI=1S/C6/c1-2-4-6-5-3-1^N Key: PXCDDPIOUAJVRE-UHFFFAOYSA-N^N
SMILES Alternating form: C1#CC#CC#C1 Cumulene form: C1=C=C=C=C=C=1
Properties
Chemical formula	C₆
Molar mass	72.066 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Benzotriyne or cyclo[6]carbon is a hypothetical compound, an allotrope of carbon with molecular formula C₆. The molecule is a ring of six carbon atoms, connected by alternating triple and single bonds.^[1] It is, therefore, a potential member of the cyclo[n]carbon family.

There have been a few attempts to synthesize benzotriyne, e.g. by pyrolysis of mellitic anhydride,^[2] but without success as of 2011^[update]. Calculations suggest that the alternative cyclic cumulene structure, called cyclohexahexaene, is the potential energy minimum of the cyclo[6]carbon framework. It is unclear whether this second structure is an isomer or a limiting resonance structure.^[3]

References

^ Adamson, George A.; Rees, Charles W. (1996). "Towards the total synthesis of cyclo[n]carbons and the generation of cyclo[6]carbon". J. Chem. Soc., Perkin Trans. 1 (13): 1535–1543. doi:10.1039/P19960001535.
^ Fields, Ellis K.; Meyerson, Seymour (October 1966). "Arynes by Pyrolysis of Acid Anhydrides". J. Org. Chem. 31 (10): 3307–3309. doi:10.1021/jo01348a046.
^ Zahradník, Rudolf; Hobza, Pavel; Burcl, Rudolf; Andes Hess, B. (October 1994). "Strained unsaturated molecules. Theoretical study of acyclic and cyclic cumulenes and acetylenes". Journal of Molecular Structure: THEOCHEM. 313 (3): 335–349. doi:10.1016/0166-1280(94)85015-1.