Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 03:47, 20 August 2011 editCitation bot 1 (talk | contribs)Bots130,044 editsm Misc citation tidying. You can use this bot yourself. Report bugs here.← Previous edit		Latest revision as of 10:34, 1 March 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,057 edits Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. Add: s2cid, bibcode. | Use this tool. Report bugs. | #UCB_Gadget
(46 intermediate revisions by 31 users not shown)
Line 1:		Line 1:
			{{cs1 config|name-list-style=vanc}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 414437161
			| Watchedfields = changed
		⚫	| verifiedrevid = 445765631
	| Name = Triptycene		| Name = Triptycene
	| ImageFileL1 = Triptycene.svg		| ImageFile = Triptycene.svg
	| ImageSizeL1 = 150px		| ImageSize = 180px
	| ImageNameL1 = triptycene		| ImageAlt = Skeletal formula
	| ImageFileR1 = Triptycene3D.png		| ImageFile1 = Triptycene-3D-spacefill.png
	| ImageSizeR1 = 150px		| ImageSize1 = 180px
			| ImageAlt1 = Space-filling model
			| PIN = 9,10-Dihydro-9,10-benzenoanthracene
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|??}}
	| CASNo = 477-75-8		| CASNo = 477-75-8
⚫	| SMILES = C12=CC=CC=C1C3C5=C<br />(C=CC=C5)C2C4=C3C=CC=C4
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = CL32869MEP
			| PubChem = 92764
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 83742
			| EINECS = 207-519-3
		⚫	| SMILES = C12=CC=CC=C1C3C5=C(C=CC=C5)C2C4=C3C=CC=C4
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/C20H14/c1-2-8-14-13(7-1)19-15-9-3-5-11-17(15)20(14)18-12-6-4-10-16(18)19/h1-12,19-20H
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = NGDCLPXRKSWRPY-UHFFFAOYSA-N
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	| Formula = C<sub>20</sub>H<sub>14</sub>		| C = 20
	| MolarMass = 254.33 g/mol		| H = 14
	| MeltingPt = 252 - 256 °C		| MeltingPtC = 252 to 256
	| BoilingPt =		| BoilingPtC = 371.8
	| Density =		| Density = 1.197 g/cm<sup>3</sup>
	}}		}}
	}}		}}
			'''Triptycene''' is an ], the simplest ] molecule with the formula C<sub>2</sub>H<sub>2</sub>(C<sub>6</sub>H<sub>4</sub>)<sub>3</sub>. It is a white solid that is soluble in organic solvents. The compound has a ] configuration with D<sub>3h</sub> ]. It is named after the medieval three-piece art panel, the ].<ref name=Bartlett/> Several substituted triptycenes are known. ]s are structurally related. Due to the rigid framework and three-dimensional geometry, derivatives of triptycene have been well researched.<ref>{{Cite journal|doi=10.1246/cl.2010.658|title = Triptycene Derivatives: Synthesis and Applications|journal = Chemistry Letters|volume = 39|issue = 7|pages = 658–667|year = 2010|last1 = Zhao|first1 = Liwei|last2 = Li|first2 = Zhong|last3 = Wirth|first3 = Thomas}}</ref>
	'''Triptycenes''' are a class of ]s. The parent compound '''triptycene''' is the ] product of ] and ]. The compound has a ] configuration with D<sub>3h</sub> ]. ]s are conceptually related compounds.
⚫	The hydrocarbon framework is very rigid and triptycene and triptycene derivatives such as triptycene quinones <ref>''Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione Spyros Spyroudis'' and Nikoletta Xanthopoulou ] '''2003''' (vi) 95-105 </ref> are therefore incorporated in many ] as a ] for instance in ]s <ref>{{cite journal |author=Kelly TR, De Silva H, Silva RA |title=Unidirectional rotary motion in a molecular system |journal=Nature |volume=401 |issue=6749 |pages=150–2 |year=1999 |month=September |pmid=10490021 |doi= 10.1038/43639|url=http://www.nature.com/nature/journal/v401/n6749/abs/401150a0.html |accessdate=2008-07-16}}</ref> or as a ] for example in this ]:<ref>{{cite journal |author=Bini L, Müller C, Wilting J, von Chrzanowski L, Spek AL, Vogt D |title=Highly selective hydrocyanation of butadiene toward 3-pentenenitrile |journal=J. Am. Chem. Soc. |volume=129 |issue=42 |pages=12622–3 |year=2007 |month=October |pmid=17902667 |doi=10.1021/ja074922e}}</ref><ref>In this reaction the substrate is ],the reagent ], the catalyst ] and the ligand a ] ] with a large ] on a trypticene scaffold</ref>
			==Synthesis==
⚫	:]
			The parent triptycene was first prepared in 1942 by a multistep method.<ref name=Bartlett>{{cite journal | last1 = Bartlett | first1 = Paul D. |author1-link= Paul Doughty Bartlett | last2 = Ryan | first2 = M. Josephine | last3 = Cohen | first3 = Saul G. | year = 1942 | title = Triptycene (9,10-''o''-Benzenoanthracene) | journal = J. Am. Chem. Soc. | volume = 64 | issue = 11 | pages = 2649–2653 | doi = 10.1021/ja01263a035 }}</ref> It can also be prepared in one step in 28% yield from the ] of ] and ].<ref>{{cite journal | last1 = Wittig | first1 = George | year = 1959 | title = Triptycene | journal = Org. Synth. | volume = 39 | page = 75 | doi = 10.15227/orgsyn.039.0075 }}</ref> In this method, benzyne is generated by the reaction of magnesium and 2-bromofluorobenzene.
			==Derivatives and applications==
		⚫	The hydrocarbon framework is very rigid and triptycene derivatives such as triptycene ]s<ref>{{ cite journal | title = Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione |vauthors=Spyroudis S, Xanthopoulou N | journal = ] | year = 2003 | volume = 2003 | issue = vi | pages = 95–105 | url = http://www.arkat-usa.org/ark/journal/2003/I06_Varvoglis/AV-630A/630A.pdf |doi=10.3998/ark.5550190.0004.612 | doi-access = free }}</ref> are therefore incorporated in many ] as a ] for various applications, such as ]s<ref>{{cite journal |vauthors=Kelly TR, De Silva H, Silva RA | title = Unidirectional rotary motion in a molecular system | journal = Nature | volume = 401 | issue = 6749 | pages = 150–152 |date=September 1999 | pmid = 10490021 | doi = 10.1038/43639 | bibcode = 1999Natur.401..150K | s2cid = 4351615 }}</ref> or ]s.
			For example, a bis(diphenylphosphino) derivative was used as a ] on ] in a highly selective ] reaction of ].<ref>{{cite journal |vauthors=Bini L, Müller C, Wilting J, von Chrzanowski L, Spek AL, Vogt D | title = Highly selective hydrocyanation of butadiene toward 3-pentenenitrile | journal = J. Am. Chem. Soc. | volume = 129 | issue = 42 | pages = 12622–12623 |date=October 2007 | pmid = 17902667 | doi = 10.1021/ja074922e | hdl = 1874/26892 | hdl-access = free }}</ref>
		⚫	<!--:]-->
			The reactivity of this catalyst is attributed to the large ] of the ] ligand supported by the triptycene framework.
	==References==		==References==
Line 33:		Line 56:
	]		]
	]
	]