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Revision as of 14:01, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465247876 of page Tricyclobutabenzene for the Chem/Drugbox validation project (updated: '').		Latest revision as of 19:29, 27 October 2022 edit Citation bot (talk | contribs)Bots5,428,575 edits Misc citation tidying. | Use this bot. Report bugs. | Suggested by AManWithNoPlan | #UCB_CommandLine
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{Chembox		{{Chembox
	| verifiedrevid = 449122043		| verifiedrevid = 470613881
	| ImageFile = Tricyclobutabenzene-from-xtal-1994-3D-balls.png		| ImageFile = Tricyclobutabenzene-from-xtal-1994-3D-balls.png
	| ImageSize =		| ImageSize =
			| PIN = Tetracyclododeca-1,5,9-triene
	| IUPACName =
	| OtherNames =		| OtherNames =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 126777		| ChemSpiderID = 126777
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	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = MTPUNWSZJLTTLU-UHFFFAOYSA-N		| StdInChIKey = MTPUNWSZJLTTLU-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|??}}		| CASNo_Ref = {{cascite|correct|pubchem}}
	| CASNo =		| CASNo = 60323-52-6
	| PubChem = 143698		| PubChem = 143698
	| SMILES = c12c4c(c3c(c1CC2)CC3)CC4		| SMILES = c12c4c(c3c(c1CC2)CC3)CC4
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=12 | H=12
	| Formula = C<sub>12</sub>H<sub>12</sub>
	| MolarMass = 156.22&nbsp;g&nbsp;mol<sup>−1</sup>
	| Appearance =		| Appearance =
	| Density =		| Density =
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	| BoilingPt =		| BoilingPt =
	| Solubility = }}		| Solubility = }}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
	| Autoignition = }}		| AutoignitionPt = }}
	}}		}}
			'''Tricyclobutabenzene''' is an ] consisting of a ] core with three ] rings fused onto it. This compound and related compounds are studied in the laboratory because they are often displaying unusual ]s and because of their unusual reactivity. Tricyclobutabenzenes are ]s of ]s and form an ] with them.
			The parent tricyclobutabenzene (C<sub>12</sub>H<sub>12</sub>) was first ] in 1979<ref>''Tricyclobutabenzene'' Wutichai Nutakul, Randolph P. Thummel, Austin D. Taggart ]; '''1979'''; 101(3); 770-771. {{doi|10.1021/ja00497a064}}</ref> by the following sequence:<ref>Reaction sequence: ] of cyclobutene ] followed by ] with dimethylcyclobutene-1,2-dicarboxylate, followed by ] ] to di] with ] in ] followed by ] and ] with ]</ref><ref>''Poly-Oxygenated Tricyclobutabenzenes via Repeated Cycloaddition of Benzyne and Ketene Silyl Acetal'' Toshiyuki Hamura, Yousuke Ibusuki, Hidehiro Uekusa, Takashi Matsumoto, and Keisuke Suzuki]; '''2006'''; 128(11) pp 3534 - 3535; {{doi|10.1021/ja0602647}}</ref> This compound is stable up to {{convert|250|C}}.
			:]
			A polyoxygenated tricyclobutabenzene with an extraordinary ] of 160 ] for the bond connecting two carbonyl groups{{Ref|Hamura}} by the following sequence:<ref>Reaction sequence: the key step is a ] between an ] formed from the iodotriflate by action of ] and a ketene silyl acetal. The silyl acetal is then converted to a ] group by ] and the remaining ] groups by reaction with ]</ref>
			:]
			An ordinary bond of this type is only 148 pm and for comparison the C-C bond in ] is 154 pm long. On the other hand, no change is recorded in the aromatic bond length alternation.
			Similar chemistry yielded the six-fold ketone ] C<sub>12</sub>O<sub>6</sub>, which happens to be a novel ].<ref>''Dodecamethoxy- and Hexaoxotricyclobutabenzene: Synthesis and Characterization'' Toshiyuki Hamura, Yousuke Ibusuki, Hidehiro Uekusa, Takashi Matsumoto, Jay S. Siegel, Kim K. Baldridge, and Keisuke Suzuki ]; '''2006'''; 128(31) pp 10032 - 10033; {{doi|10.1021/ja064063e}}</ref> A key starting material is the iodo triflate depicted below which is a ] ].
			:]
			==See also==
			* ]
			* ]
			* ]
			* ]
			* ] where the rings are fused
			==References==
			{{Reflist}}
			{{PAHs}}
			]
			]
			]
			]