chembox verifiedrevid 437333762 ImageFileL1 Bullvalene.svg ImageSizeL1 100px ImageFileR1 Bullvalene from xtal 3D balls.png ImageSizeR1 120px IUPACName Tricyclo 3.3.2.0 sup 2,8 sup deca 3,6,9 triene OtherNames Bullvalen Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 120549 InChI 1 C10H10 c1 4 8 9 5 2 7 1 3 6 10 8 9 h1 10H InChIKey UKFBVTJTKMSPMI UHFFFAOYAK StdInChI Ref stdinchicite correct chemspider StdInChI 1S C10H10 c1 4 8 9 5 2 7 1 3 6 10 8 9 h1 10H StdInChIKey Ref stdinchicite correct chemspider StdInChIKey UKFBVTJTKMSPMI UHFFFAOYSA N CASNo 1005 51 2 PubChem 136796 SMILES C 2 C C 1 C C C3C C C 1 C 23 Section2 Chembox Properties Formula C sub 10 sub H sub 10 sub MolarMass 130.19 g mol Appearance Density MeltingPt 96 C BoilingPt decomposition at about 400 C Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Bullvalene is a hydrocarbon with the chemical formula C sub 10 sub H sub 10 sub with the unusual property that the chemical bond s making up the molecule are constantly rearranging as in fluxional molecule s. For this reason bullvalene is extensively studied in organic chemistry . Origin of the name The name bullvalene ... last1 Ault first1 Addison year 2001 title The Bullvalene Story. The Conception of Bullvalene, a Molecule ... York, 1972 p 131. ref Stereodynamics The bullvalene molecule is a cyclopropane platform with three vinyl arms conjoined at a methine group. As a fluxional molecule , bullvalene subject to degenerate ... timescale. The number of possible valence tautomer s is 10 Factorial 3 1,209,600. Image Bullvalene rearrangements.png thumb left 500px Scheme 1. Five of the bullvalene tautomers and some Cope ... of bullvalene have been examined by dynamic NMR spectroscopy. For example, the proton NMR spectrum ... group in one of the arms in bullvalene is replaced by a ketone keto methylene group. In this way .... References reflist Category Hydrocarbons Category Dienes de Bullvalen it Bullvalene ... more details
The molecular formula C sub 8 sub H sub 8 sub may refer to Barrelene Benzocyclobutene Cubane Cuneane Cyclooctatetraene Bullvalene Semibullvalene Semibullvalene Styrene MolFormDisambig fr C8H8 it C8H8 nl C8H8 ... more details
DISPLAYTITLE C sub 10 sub H sub 10 sub C sub 10 sub H sub 10 sub may refer to Compounds sharing the molecular formula Bullvalene Cyclodecapentaene Dilin Divinylbenzene Molecular formula disambiguation C sub 10 sub H sub 10 sub fr C10H10 nl C10H10 ... more details
A polyquinane and polyquinene is a saturated or Unsaturated compound unsaturated , respectively, polycyclic hydrocarbon consisting of fused five membered rings ref Gold Book definition http goldbook.iupac.org P04751 plain.html Link ref . The simplest member is the bicyclic compound bicyclo 3.3.0 octane. Other members are triquinacene and dodecahedrane . Triquinacene Image Triquinacene.png right 300px triquinacene The compound triquinacene tricyclo 5.2.1. 0 sup 4,10 sup deca 2,5,8 triene is the second member of a family of polyquinenes. It was synthesized in 1964 in the group of Robert Burns Woodward R. B. Woodward ref cite journal title Triquinacene author Robert Burns Woodward R. B. Woodward , T. Fukunaga, R. C. Kelly J. Am. Chem. Soc. year 86 issue 15 pages 3162 3164 doi 10.1021 ja01069a046 journal Journal of the American Chemical Society volume 86 ref in connection with its suspected homoaromaticity homoaromatic properties although it was found to have no such properties , and also as part of a failed attempt to synthesize the then elusive and much coveted compound dodecahedrane . Unlike the related pentacene , triquinacene is stable, and has a melting point of 18 C. The final step of its synthesis is a Cope elimination . Image TriquinaceneSynthesis.png 400px triquinacene synthesis Woodward 1965 See also Fused 6 membered rings the acene s triquinacene is Isomeric with bullvalene , diisopropenyldiacetylene References reflist Category Polycyclic nonaromatic hydrocarbons ... more details
Infobox person name Maitland Jones, Jr image Maitland Jones.jpg birth date Birth date and age mf yes 1937 11 23 other names Prof. Jones occupation Chemist website http www.nyu.edu cas prehealth postbacc maitland jones bio.html Maitland Jones Website Maitland Jones, Jr born November 23, 1937 is an internationally renowned United States American experimental chemist , based primarily at Princeton University . He received tenure in 1973. Jones s field of expertise is reactive intermediates, with particular emphasis on carbene s. He has published extensively in the field of organic chemistry , particularly focusing on the mechanism of molecular reactions. His interest areas include carbenes, carborane s, and heterocycle s. Over the course of almost forty years, he and his research group have published 225 papers, averaging some five papers per year or one paper per active group member per year. Jones is also the author of a Organic Chemistry texts. He is sometimes credited with the naming of bullvalene . As of fall 2007, Jones teaches Organic Chemistry at New York University . NOTOC Textbooks Organic Chemistry , Jones, M., Jr. W. W. Norton, New York, 1997 Instructor s Manual and Supplementary Problems Set for Organic Chemistry , Jones, M., Jr., Ovaska, T. W. W. Norton, New York, 1997. Study Guide for Organic Chemistry , Jones, M. Jr. Gingrich, H. L. W. W. Norton, New York, 1997 Study Guide for Organic Chemistry , Third Edition, Jones, M. Jr. Gingrich, H. L. W. W. Norton, New York, 2004 Research articles http www.princeton.edu mjjr Pubs.html Maitland Jones, Jr., et al. Academic experience Postdoctoral Fellow, Yale University 1963 Postdoctoral Fellow, University of Wisconsin Madison 1963&ndash 1964 Instructor in Chemistry, Princeton University 1964&ndash 1966 Assistant Professor, Princeton University 1966&ndash 1970 Visiting Assistant Professor, Columbia University 1969&ndash 1970 Associate Professor, Princeton University 1970&ndash 1973 Professor, Princeton University 19 ... more details
The Cope rearrangement is an extensively studied organic reaction involving the sigmatropic rearrangement 3,3 sigmatropic rearrangement of 1,5 dienes. ref Arthur C. Cope et al. J. Am. Chem. Soc. 1940 , 62 , 441. ref ref Rhoads, S. J. Raulins, N. R. Org. React. 1975 , 22 , 1 252. Review ref ref Hill, R. K. Comp. Org. Syn. 1991 , 5 , 785 826. ref ref Wilson, S. R. Org. React. 1993 , 43 , 93 250. Review ref It was developed by Arthur C. Cope . For example 3 methyl 1,5 hexadiene heated to 300 C yields 1,5 heptadiene. Image Cope Rearrangement Scheme.png center 400px The Cope rearrangement of 3 methyl 1,5 hexadiene The Cope rearrangement causes the Fluxional molecule fluxional states of the molecules in the bullvalene family. Mechanism Although the Cope rearrangement is concerted reaction concerted and pericyclic , it can also be considered to go via a transition state that is energetically and structurally equivalent to a radical chemistry diradical . This is an alternative explanation which remains faithful to the uncharged nature of the Cope transition state, while preserving the principles of orbital symmetry. This also explains the high energy requirement to perform a Cope rearrangement. Although illustrated in the chair conformation , the Cope can also occur with cyclohexadienes in the boat conformation. Image Cope.png The above description of the transition state is not quite correct. It is currently generally accepted that the Cope rearrangement follows an allowed concerted route through a homoaromatic transition state and not a diradical. That is unless the potential energy surface is perturbed to favor the diradical. ref Williams, R. V., Chem. Rev. 2001, 101 5 , 1185 1204. ref Examples The rearrangement is widely used in organic synthesis. It is symmetry allowed when it is suprafacial on all components. The transition state of the molecule passes through a boat or chair like transition state. An example of the Cope rearrangement is the expansion of a cyclobutane ... more details
a Association football ball football . valign top Bullvalene valign top Image Bullvalene.svg right 100px Bullvalene C sub 10 sub H sub 10 sub tricyclo 3.3.2.0 sup 2,8 sup deca 3,6,9 triene C sub 10 sub ... title The Bullvalene Story. The Conception of Bullvalene, a Molecule That Has No Permanent Structure ... more details
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