340-19-2Relevant academic research and scientific papers
Microwave flash pyrolysis: C9h8 interconversions and dimerisations
Ajaz, Aida,Voukides, Alicia C.,Cahill, Katharine J.,Thamatam, Rajesh,Skraba-Joiner, Sarah L.,Johnson, Richard P.
, p. 1301 - 1308 (2014/11/07)
The pyrolysis of 2-ethynyltoluene, indene, fluorene, and related compounds has been studied by sealed tube microwave flash pyrolysis (MFP), in concert with modelling of putative mechanistic pathways by density functional theory (DFT) computations. In the MFP technique, samples are admixed with graphite and subjected to intense microwave power (150-300 W) in a quartz reaction tube under a nitrogen atmosphere. The MFP reaction of 2-ethynyltoluene gave mostly indene, the product of a Roger Brown rearrangement (1,2-H shift to a vinylidene) followed by insertion. An additional product was chrysene, the likely result of hydrogen atom loss from indene followed by dimerisation. The intermediacy of dimeric bi-indene structures was supported by pyrolysis of bi-indene and by computational models. Benzo[a]anthracene and benzo[c]phenanthrene are minor products in these reactions. These are shown to arise from pyrolysis of chrysene under the same MFP conditions. MFP reaction of fluorene gave primarily bi-fluorene, bifluorenylidene, and dibenzochrysene, the latter derived from a known Stone-Wales rearrangement.
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%).
