203-33-8Relevant articles and documents
A three-step process to facilitate the annulation of polycyclic aromatic hydrocarbons
Martin, Sara E.,Streeter, Matthew D.,Jones, Laurel L.,Klepfer, Matthew S.,Atmatzidis, Kyriakos,Wille, Kristen D.,Harrison, Sean A.,Hoegg, Edward D.,Sheridan, Heather M.,Kramer, Stephanie,Parrish, Damon A.,Amick, Aaron W.
, p. 8324 - 8330 (2015/03/18)
A new efficient three-step process to annulate polycyclic aromatic hydrocarbons (PAHs) has been developed, providing access to PAHs with saturated rings that under current chemical methods would be difficult to produce in an efficient manner. This method relies on a palladium-catalyzed cross-coupling reaction of various brominated PAHs with cyclohexanone to yield α-arylated ketones, which are converted to regiospecific vinyl triflates and cyclized by a palladium-catalyzed intramolecular arene-vinyl triflate coupling to produce PAHs with incorporated saturated rings or "tetrahydroindeno-annulated" PAHs.
A new Suzuki-Heck-type coupling cascade: Indeno[1,2,3]-annelation of polycyclic aromatic hydrocarbons
Wegner, Hermann A.,Scott, Lawrence T.,De Meijere, Armin
, p. 883 - 887 (2007/10/03)
Under palladium catalysis, o-bromobenzeneboronic acid can be coupled with 1-bromonaphthalene (6) and with oligocyclic bromoarenes to furnish indeno-annelated polycyclic aromatic hydrocarbons 1-4 and 25 in a single operation in moderate to good yields (27-87%). Alternatively, o-dibromoarenes and 1,2-dibromocycloalkenes can be cross-coupled with 1-naphthaleneboronic acid under the same conditions to yield analogous products (6-87%), and indenocorannulene (19) can be prepared likewise in a single step from pinacol corannuleneboronate (18) (40%).
Thermolysis and photolysis of 1-substituted triptycenes. Divergent fragmentation pathways of the triptycyl skeleton
Tomioka, Hideo,Nakajima, Junichi
, p. 563 - 569 (2007/10/03)
While thermolysis of 1-benzyltriptycene 1a in the gas phase at 600°C/10-4 mmHg did not result in any appreciable decomposition, similar pyrolysis of compounds 1 bearing various substituents (X) at the benzyl methylene (1b-d) underwent smooth decomposition to give 8-benzylbenz[a]aceanthrylene 2. The reaction is explained in terms of homolysis of the C-X bond followed by triptycyl ring cleavage in the resulting benzyl radical 7. Generation of radical 7 in solution, however, did not result in a similar ring-opening reaction. Irradiation of compounds 1, on the other hand, afforded norcaradienes 3 almost exclusively, obviously as a result of di-π-methane rearrangement. No products resulting from a carbene species proposed to be involved in the di-π-methane reaction of triptycenes were detected. Thermolysis of compounds 3 gave not only compound 2 but also benz[a]aceanthrylene 4 and benz[a]indeno[1,2,3-cd]azulene 5 whose compositions were found to be sensitive to both the substituent (X) and the thermolysis temperature. Mechanisms of the reactions are discussed in terms of the relationship between the thermal and photochemical fragmentations.
