17509-84-1Relevant academic research and scientific papers
The elusive benzocyclobutenylidene: A combined computational and experimental attempt
Nicolaides,Matsushita,Yonezawa,Sawai,Tomioka,Stracener,Hodges,McMahon
, p. 2870 - 2876 (2007/10/03)
Ab initio and density functional theory calculations predict that benzocyclobutenylidene (1) has a singlet ground state in contrast to the parent phenylcarbene and many other simply substituted arylcarbenes. Calculations also predict that 1 should lie in a relatively deep potential well, while its triplet state is 14.5 kcal mol-1 higher in energy. However, attempts to observe 1 directly by photolysis of two different nitrogenous precursors were not successful. Irradiation of diazobenzocyclobutene (7) (λ > 534 nm or λ > 300 nm) or azibenzocyclobutene (10) (λ > 328 nm) in Ar matrixes at 10 K leads to the formation of the strained cycloalkyne 7-methylenecyclohepta-3,5-dien-1-yne (3). 13C-Labeled 3 was also prepared in a similar manner. There is very good agreement between experimental IR spectra and computationally derived harmonic vibrational frequencies for 3 and [13C]-3 and excellent agreement between observed and calculated isotopic shifts. Prolonged short-wavelength irradiation converts 3 into benzocyclobutadiene (5). Phenylacetylene (6) and benzocyclobutadiene dimer (11) were identified as products arising from flash vacuum pyrolysis of diazirine 10 at 500 °C.
Flow-Vacuum Pyrolysis of Polycyclic Compounds, 6. Pyrolysis of Dibenzo 8 Hydrocarbons
Banciu, Mircea D.,Stanescu, Michaela D.,Petride, Aurica,Parvulescu, Luminitza,Pop, Mircea
, p. 2513 - 2518 (2007/10/02)
The flow-vacuum pyrolysis of dibenzo 8 hydrocarbons 2, 3, 4, and 5 are studied at 1 Torr and in the temperature range between 400 and 650 deg C.The following new transformations have been observed: 24, 2-->5, 3-->5, 34, 3-->2, 5-->11, the last three presenting analogies in the 8 and/or benzo 8 series.A reaction mechanism is suggested. - Key Words: Dibenzo 8 hydrocarbons / Flow-vacuum pyrolysis
Synthesis and cycloreversion of benzocyclobutene- and benzocyclobutadiene-anthracene adducts
Okada,Kawai,Oda
, p. 257 - 260 (2007/10/02)
The [4+2]-cycloadducts of anthracene and benzocyclobutene or benzocyclobutadiene were synthesized and their cycloreversion was investigated.
FLOW-VACUUM PYROLYSIS OF DIBENZOTRICYCLO2,5>-DECA-3,7,9-TRIENE (syn-DIBENZONENITZESCU'S HYDROCARBON) AND OF TRIBENZOTRICYCLO2,5>DECA-3,7,9-TRIENE (TRIBENZO-NENITZESCU'S HYDROCARBON)
Banciu, Mircea D.,Pop, Mircea,Petride, Aurica,Stanescu, Michaela Dina
, p. 907 - 916 (2007/10/03)
Retro-diene reactions are the favoured pathways in the flow-vacuum pyrolysis of both title hydrocarbons 6 and 7. The main reactions products in the pyrolysis of 6 are: the angular dimer 17 of benzocyclobutene (Cava's dimer), naphthalene, dibenzocyclooctene and benzobiphenylene. From the pyrolysis products of 7, anthracene, Cava's dimer 17 and dibenzocyclooctene were identified. The reaction mechanisms are discussed and a comparison with pyrolyses of related Nenitzescu's hydrocarbons is presented.
