195-19-7Relevant articles and documents
Aromatic hydrocarbon growth from indene
Lu, Mingming,Mulholland, James A.
, p. 625 - 633 (2001)
Aromatic hydrocarbon growth from indene (C9H8), which contains the five-membered ring cyclopentadienyl moiety, was investigated experimentally in a 4 s flow reactor over a temperature range 650-850°C. Major products observed were three C18H12 isomers (chrysene, benz[a]anthracene and benzo[c]phenanthrene), two C17H12 isomers (benzo[a]fluorene and benzo[b]fluorene), and two C10H8 isomers (naphthalene and benzofulvene). Reaction pathways to these products are proposed. Indenyl radical addition to indene produces a resonance-stabilized radical intermediate which further reacts by one of two routes. Rearrangement by intramolecular addition produces a bridged structure that leads to the formation of C17H12 and C10H8 products. Alternatively, β scission produces biindenyl, which leads to the formation of C18H12 products by a ring condensation mechanism analogous to that proposed for cyclopentadiene-to-naphthalene conversion. Temperature dependencies of both the partitioning between these two routes and the product isomer distributions are consistent with thermochemical modeling using semi-empirical molecular orbital methods. The results further illustrate the role of resonance-stabilized radical rearrangement in aromatic growth and condensation of systems with cyclopentadienyl moieties.
Synthesis of 1-(2-ethynyl-6-methylphenyl)- and 1-(2-ethynyl-6-methoxyphenyl)-naphthalene and their cyclization
Storch, Jan,?ermák, Jan,Karban, Jind?ich
, p. 6814 - 6816 (2007)
A Suzuki cross-coupling reaction of hindered 2-bromo-1-trimethylsilylethynylbenzenes with 1-naphthaleneboronic acid yielding (2-ethynylphenyl)naphthalenes has been achieved. Their subsequent cyclization was carried out, giving benzo[c]phenanthrenes, without the use of photochemical procedures.
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Newmann,Joshel
, (1940)
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Cook
, p. 2524,2527 (1931)
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Water Docking Bias in [4]Helicene
Domingos, Sérgio R.,Martin, Kévin,Avarvari, Narcis,Schnell, Melanie
supporting information, p. 11257 - 11261 (2019/07/12)
We report on the one- and two-water clusters of [4]helicene, the smallest polycyclic aromatic hydrocarbon with a helical sense, which were captured in the gas phase using high-resolution rotational spectroscopy. The structures of the complexes are unambiguously revealed using microwave spectra of isotopically enriched species. In the one-water cluster, the apparent splitting pattern is consistent with a tunneling motion that encompasses an exchange of strongly and weakly bonded water hydrogens. This motion is “locked” in the two-water cluster. The relevant intermolecular contacts, symmetry, and aromaticity effects are unveiled for the microsolvated chiral topologies. These observations entail the first glance at the structures and internal dynamics of the water binding motifs of a chiral polycyclic aromatic hydrocarbon.
Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes
Chen, Ming,Zhao, Xinxin,Yang, Chao,Wang, Yanpei,Xia, Wujiong
, p. 12022 - 12026 (2017/03/01)
Reported herein is further insight into the photochemical behaviour of 3-aryl-N-(arylsulfonyl)-propiolamides, which provides a straightforward way to access meaningful phenanthrenes. Mechanistic investigation indicated that aryl migration, C-C coupling, 1,3-hydrogen shift, desulfonylation and elimination were involved in the process. Moreover, this protocol allowed for scale-up using a flow reactor.
Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis
McAtee, Christopher C.,Riehl, Paul S.,Schindler, Corinna S.
supporting information, p. 2960 - 2963 (2017/03/11)
Polycyclic aromatic hydrocarbons are important structural motifs in organic chemistry, pharmaceutical chemistry, and materials science. The development of a new synthetic strategy toward these compounds is described based on the design principle of iron(III)-catalyzed carbonyl-olefin metathesis reactions. This approach is characterized by its operational simplicity, high functional group compatibility, and regioselectivity while relying on FeCl3 as an environmentally benign, earth-abundant metal catalyst. Experimental evidence for oxetanes as reactive intermediates in the catalytic carbonyl-olefin ring-closing metathesis has been obtained.
