Tetraethynylmethane

Tetraethynylmethane
Names
	Preferred IUPAC name 3,3-diethynylpenta-1,4-diyne
Identifiers
3D model (JSmol)	Interactive image;
PubChem CID	14934811;
	InChI InChI=1S/C9H4/c1-5-9(6-2,7-3)8-4/h1-4H Key: JVMGUYOVBKXTJL-UHFFFAOYSA-N;
	SMILES C#CC(C#C)(C#C)C#C;
Properties
Chemical formula	C9H4
Molar mass	112.131 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

Tetraethynylmethane is an organic compound with formula C₉H₄, consisting of four ethynyl groups bonded to a central carbon atom. It is an alkyne, and one of the most compact possible hydrocarbons. It has been synthesised for potential applications in the synthesis of polymeric forms of carbon such as synthetic diamond and fullerenes.^[1]^[2]^[3]^[4]^[5]^[6]

References[edit]

^ Feldman KS, Kraebel CM, Parvez M (May 1993). "Tetraethynylmethane". Journal of the American Chemical Society. 115 (9): 3846–3847. doi:10.1021/ja00062a089.
^ Feldman KS, Weinreb CK, Youngs WJ, Bradshaw JD (October 1994). "Preparation and some subsequent transformations of tetraethynylmethane". Journal of the American Chemical Society. 116 (20): 9019–9026. doi:10.1021/ja00099a020.
^ Feldman KS, Mareska DA, Weinreb CK, Chasmawala M (January 1996). "Preliminary studies towards crosslinking polymerizations with tetraethynylmethane and its derivatives: evidence for unusually facile alkyne hydration". Chemical Communications (7): 865–866. doi:10.1039/CC9960000865.
^ Amemiya R, et al. One-Step Synthesis of Triethynylvinylmethanes and Tetraethynylmethanes by GaCl 3 -Promoted Diethynylation of 1,4-Enynes and 1,4-Diynes. Journal of the American Chemical Society 2005; 127(23):8252-3. doi:10.1021/ja051416l
^ Zhao Z, et al. A 3D Organically Synthesized Porous Carbon Material for Lithium-Ion Batteries. Angewandte Chemie 2018; 57(37): 11952-11956. doi:10.1002/anie.201805924
^ Kilde MD, Murray AH, Andersen CL, et al. Synthesis of radiaannulene oligomers to model the elusive carbon allotrope 6,6,12-graphyne. Nat Commun 2019;10:3714. doi:10.1038/s41467-019-11700-0

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[1] Feldman KS, Kraebel CM, Parvez M (May 1993). "Tetraethynylmethane". Journal of the American Chemical Society. 115 (9): 3846–3847. doi:10.1021/ja00062a089.

[2] Feldman KS, Weinreb CK, Youngs WJ, Bradshaw JD (October 1994). "Preparation and some subsequent transformations of tetraethynylmethane". Journal of the American Chemical Society. 116 (20): 9019–9026. doi:10.1021/ja00099a020.

[3] Feldman KS, Mareska DA, Weinreb CK, Chasmawala M (January 1996). "Preliminary studies towards crosslinking polymerizations with tetraethynylmethane and its derivatives: evidence for unusually facile alkyne hydration". Chemical Communications (7): 865–866. doi:10.1039/CC9960000865.

[4] Amemiya R, et al. One-Step Synthesis of Triethynylvinylmethanes and Tetraethynylmethanes by GaCl 3 -Promoted Diethynylation of 1,4-Enynes and 1,4-Diynes. Journal of the American Chemical Society 2005; 127(23):8252-3. doi:10.1021/ja051416l

[5] Zhao Z, et al. A 3D Organically Synthesized Porous Carbon Material for Lithium-Ion Batteries. Angewandte Chemie 2018; 57(37): 11952-11956. doi:10.1002/anie.201805924

[6] Kilde MD, Murray AH, Andersen CL, et al. Synthesis of radiaannulene oligomers to model the elusive carbon allotrope 6,6,12-graphyne. Nat Commun 2019;10:3714. doi:10.1038/s41467-019-11700-0

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