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Pure Appl. Chem., 1996, Vol. 68, No. 2, pp. 219-224

http://dx.doi.org/10.1351/pac199668020219

Thermal generation and (inter)conversion of (multi) cyclopenta-fused polycyclic aromatic hydrocarbons

L. W. Jenneskens, M. Sarobe and J. W. Zwikker

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  • Pastor Michael B., Kuhn Ariel J., Nguyen Phuong T., Santander Mitchell V., Castro Claire, Karney William L.: Hydrogen shifts and benzene ring contractions in phenylenes. J. Phys. Org. Chem. 2013, 26, 750. <http://dx.doi.org/10.1002/poc.3126>
  • Balaban Alexandru T.: Bond-switch defects in carbon allotropes: Stone-Wales and connected exchange. Chemical Physics Letters 2013, 566, 50. <http://dx.doi.org/10.1016/j.cplett.2013.02.060>
  • Zhou Jianshi, Ma Quanling, Zong Zhimin, Wei Xianyong: Separation of acearylenes from high-temperature coal tar. Trans. Tianjin Univ. 2012, 18, 378. <http://dx.doi.org/10.1007/s12209-012-1742-5>
  • Radenković Slavko, Đurđević Jelena, Bultinck Patrick: Local aromaticity of the five-membered rings in acenaphthylene derivatives. Phys. Chem. Chem. Phys. 2012, 14, 14067. <http://dx.doi.org/10.1039/c2cp41472d>
  • Stanković Sonja, Marković Svetlana, Gutman Ivan, Sretenović Silva: Hydrogen-mediated Stone-Wales isomerization of dicyclopenta[de,mn]anthracene. J Mol Model 2010, 16, 1519. <http://dx.doi.org/10.1007/s00894-010-0669-9>
  • Marković Svetlana, Stanković Sonja, Radenković Slavko, Gutman Ivan: Thermal isomerization in cyclopenta[fg]aceanthrylene. Monatshefte für Chemie 2009, 140, 153. <http://dx.doi.org/10.1007/s00706-008-0046-x>
  • Stanković Sonja, Marković Svetlana, Radenković Slavko, Gutman Ivan: Formation and isomerization of dicyclopenta[de,mn]anthracene. Electronic Structure Study. J Mol Model 2009, 15, 953. <http://dx.doi.org/10.1007/s00894-009-0453-x>
  • Ruiz-Morales Yosadara: Aromaticity in pericondensed cyclopenta-fused polycyclic aromatic hydrocarbons determined by density functional theory nucleus-independent chemical shifts and the Y-rule — Implications in oil asphaltene stability. Can J Chem 2009, 87, 1280. <http://dx.doi.org/10.1139/V09-052>
  • Todorov Petar D., Koper Carola, van Lenthe Joop H., Jenneskens Leonardus W.: Gas phase adiabatic electron affinities of cyclopenta-fused polycyclic aromatic hydrocarbons. chem phys letts 2008, 454, 30. <http://dx.doi.org/10.1016/j.cplett.2008.01.065>
  • Otero-Lobato María José, Jenneskens Leonardus W., Seinen Willem: Cyclopenta[cd]fluoranthene and its precursors in combustion exhausts: A survey of their bacterial mutagenic activity. Environ Mol Mutagen 2004, 44, 304. <http://dx.doi.org/10.1002/em.20047>
  • Jehlička Jan, Svatoš Aleš, Frank Ota, Uhlík Filip: Evidence for fullerenes in solid bitumen from pillow lavas of Proterozoic age from Mítov (Bohemian Massif, Czech Republic). Geochimica et Cosmochimica Acta 2003, 67, 1495. <http://dx.doi.org/10.1016/S0016-7037(02)01404-7>
  • Fabbri Daniele, Vassura Ivano, Sun Cheng-Gong, Snape Colin E., McRae Carole, Fallick Anthony E.: Source apportionment of polycyclic aromatic hydrocarbons in a coastal lagoon by molecular and isotopic characterisation. Mar Chem 2003, 84, 123. <http://dx.doi.org/10.1016/S0304-4203(03)00135-X>
  • Koper Carola, Jenneskens Leonardus W, Sarobe Martin: Externally-fused cyclopenta moieties in non-alternant CP-PAHs act as peri-substituents. Tetrahetron Lett 2002, 43, 3833. <http://dx.doi.org/10.1016/S0040-4039(02)00683-4>
  • Violi A, Sarofim A.F, Truong T.N: Quantum mechanical study of molecular weight growth process by combination of aromatic molecules. Combustion and Flames 2001, 126, 1506. <http://dx.doi.org/10.1016/S0010-2180(01)00268-1>
  • Nagano Yatsuhisa: Micro-combustion calorimetry of coronene. K J CHEM THERMODYN 2000, 32, 973. <http://dx.doi.org/10.1006/jcht.2000.0663>
  • Sarobe Martin, Kwint Huibert C., Fleer Theun, Havenith Remco W. A., Jenneskens Leonardus W., Vlietstra Edward J., van Lenthe Joop H., Wesseling Jolanda: Flash Vacuum Thermolysis of Acenaphtho[1,2-a]acenaphthylene, Fluoranthene, Benzo[k]- and Benzo[j]fluoranthene – Homolytic Scission of Carbon-Carbon Single Bonds of Internally Fused Cyclopenta Moieties atT ≥ 1100 °C. Eur J Org Chem 1999, 1999, 1191. <http://dx.doi.org/10.1002/(SICI)1099-0690(199905)1999:5<1191::AID-EJOC1191>3.0.CO;2-W>
  • C. Brown Roger F.: Some Developments in the High Temperature Gas Phase Chemistry of Alkynes, Arynes and Aryl Radicals. Eur J Org Chem 1999, 1999, 3211. <http://dx.doi.org/10.1002/(SICI)1099-0690(199912)1999:12<3211::AID-EJOC3211>3.0.CO;2-F>
  • Imamura Koichi, Hirayama Daigo, Yoshimura Hitoshi, Takimiya Kazuo, Aso Yoshio, Otsubo Tetsuo: Application of flash vacuum pyrolysis to the synthesis of sulfur-containing heteroaromatic systems. Tetrahetron Lett 1999, 40, 2789. <http://dx.doi.org/10.1016/S0040-4039(99)00295-6>
  • Jenneskens Leonardus W., Sarobe Martin: Prevalent Cyclopentafused Polycyclic Aromatic Hydrocarbon (CP-PAH) Combustion Effluents. Build-up and Conversion under High Temperature Conditions in the Gas Phase. Polycyclic Arom Comp 1999, 14, 169. <http://dx.doi.org/10.1080/10406639908019123>
  • Visser Tom, Sarobe Martin, Jenneskens Leonardus W., Wesseling Jolanda W.: Identification of isomeric polycyclic aromatic hydrocarbons (PAH) in pyrolysates from ethynylated PAH by gas chromatography-Fourier infrared spectroscopy. Their relevance for the understanding of PAH rearrangement and interconversion processes during combustion. Fuel Lond 1998, 77, 913. <http://dx.doi.org/10.1016/S0016-2361(97)00291-3>
  • Sarobe Martin, Kwint Huibert C., Fleer Theun, Jenneskens Leonardus W., Wesseling Jolanda: Flash vacuum thermolysis of acenaphtho[1,2-a]acenaphthylene. Thermal behaviour of a polycyclic aromatic hydrocarbon containing two abutting pentagons. Tetrahetron Lett 1998, 39, 9823. <http://dx.doi.org/10.1016/S0040-4039(98)02242-4>
  • Hammida Mohamed, Fonseca Antonio, Doome Roger, De Hoffmann Edmond, Thiry Paul A., Nagy Janos B., Grieco William J., Lafleur Arthur L., Swallow Kathleen C., Richter Henning, Taghizadeh Koli, Howard Jack B., Wornat Mary J., Vernaglia Brian A., Lafleur Arthur L., Plummer Elaine F., Taghizadeh Koli, Nelson Peter F., Li Chun-Zhu, Necula Atena, Scott Lawrence T.: C60, C60O, C70 and C70O fullerene formations in premixed benzene-oxygen flames. Symposium (International) on Combustion 1998, 27, 1663. <http://dx.doi.org/10.1016/S0082-0784(98)80007-6>
  • Lafleur Arthur L., Howard Jack B., Plummer Elaine, Taghizadeh Koli, Necula Atena, Scott Lawrence T., Swallow Kathleen C.: Identification of Some Novel Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons in Ethylene Flames. Polycyclic Arom Comp 1998, 12, 223. <http://dx.doi.org/10.1080/10406639808233840>
  • Sarobe Martin, Jenneskens Leonardus W., Wesseling Jolanda, Snoeijer Judith D., Zwikker Jan W.: Thermal Interconversions of the C16H10 Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons Fluoranthene, Acephenanthrylene and Aceanthrylene Revisited. Liebigs Ann /Recueil 1997, 1997, 1207. <http://dx.doi.org/10.1002/jlac.199719970624>
  • Sarobe Martin, van Heerbeek Rieko, Jenneskens Leonardus W., Zwikker Jan W.: Unexpected High Temperature Behaviour of 2,2′-Diethynylbiphenyl in the Gas Phase – a Precursor for Acephenanthrylene Instead of Pyrene. Liebigs Ann /Recueil 1997, 1997, 2499. <http://dx.doi.org/10.1002/jlac.199719971212>
  • Gooijer Cees, Kozin Iqor, Velthorst Nel H.: Shpol'skii spectrometry, a distinct method in environmental analysis. Microchim Acta 1997, 127, 149. <http://dx.doi.org/10.1007/BF01242719>
  • Kataoka Masahiro: Magnetic properties of dicyclopentapyrenes and their congeners. Tetrahedron 1997, 53, 12875. <http://dx.doi.org/10.1016/S0040-4020(97)00803-X>
  • Scott Lawrence T., Necula Atena: Thermal migration of an ethynyl group from one benzene ring to another by reversible vinylidene CH insertion. Tetrahetron Lett 1997, 38, 1877. <http://dx.doi.org/10.1016/S0040-4039(97)00225-6>
  • Sarobe Martin, Jenneskens Leonardus W., Wiersum Ulfert E.: Thermolysis of benzo[c]phenanthrene-5,6-dicarboxylic anhydride and 6H-benzo[cd]pyren-6-one. Entries to the combustion effluents benzo[ghi]fluoranthene and cyclopenta[cd]pyrene. Tetrahetron Lett 1997, 38, 4689. <http://dx.doi.org/10.1016/S0040-4039(97)00998-2>
  • Sarobe Martin, Jenneskens Leonardus W., Kleij Arjan, Petroutsa Maria: Migration of redundant ethynyl substituents along polycyclic aromatic hydrocarbon peripheries. Consequences for polycyclic aromatic hydrocarbon build up. Tetrahetron Lett 1997, 38, 7255. <http://dx.doi.org/10.1016/S0040-4039(97)01685-7>
  • Harvey Ronald G.: BRIDGED POLYCYCLIC AROMATIC HYDROCARBONS. A REVIEW. Org Prep Proced Int 1997, 29, 243. <http://dx.doi.org/10.1080/00304949709355197>