6134-55-0Relevant articles and documents
Nucleophilic addition to a p-benzyne derived from an enediyne: A new mechanism for halide incorporation into biomolecules
Perrin, Charles L.,Rodgers, Betsy L.,O'Connor, Joseph M.
, p. 4795 - 4799 (2007)
Biosynthesis of haloaromatics ordinarily occurs by electrophilic attack of an activated halogen species on an electron-rich aromatic ring. We now present the discovery of a new reaction whereby a nucleophilic halide anion can be attached even to an aromatic ring without activating substituents. We show that the enediyne cyclodeca-1,5-diyn-3-ene, in the presence of lithium halide and a weak acid, is converted to 1-halotetrahydronaphthalene. The kinetics are consistent with rate-limiting cyclization to a p-benzyne biradical that rapidly adds halide and is then protonated. This reaction has interesting mechanistic features and important implications for incorporation of halide into biomolecules.
13C scrambling of [5-13C]5-cyclodecynone
Wempe, Michael F.,Grunwell, John R.
, p. 6709 - 6713 (2000)
Scrambling of [5-13C]5-cyclodecynone occurs as a result of acidic conditions that preclude its rapid consumption. (C) 2000 Elsevier Science Ltd.
Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides
Nishii, Yuji,Ikeda, Mitsuhiro,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro
supporting information, p. 1621 - 1629 (2020/02/04)
A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.
New organic compounds and organic light emitting device using the same
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Paragraph 0077, (2016/10/07)
The present invention relates to a polycyclic aromatic hydrocarbon compound in which a substituted or unsubstituted C2-30 cycloalkane, or a substituted or unsubstituted C5-50 polycycloalkane is fused to a substituent of said polycyclic aromatic hydrocarbon as represented by formula (3). Furthermore, the present invention relates to an organic light emitting device comprising a first electrode, at least one organic layer and a second electrode, laminated successively, in which at least one organic layer comprises said polycyclic aromatic hydrocarbon compound.