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Titolo:
Origin of pyrene under high temperature conditions in the gas phase. The pivotal role of phenanthrene
Autore:
Sarobe, M; Jenneskens, LW; Steggink, RGB; Visser, T;
Indirizzi:
Univandsecht, Debye Inst, Dept Phys Organ Chem, NL-3584 CH Utrecht, Netherl Univ Utrecht Utrecht Netherlands NL-3584 CH NL-3584 CH Utrecht, Netherl Natl,Inst Publ Hlth & Environm, Lab Organ Analyt Chem, NL-3720 BA Bilthoven Natl Inst Publ Hlth & Environm Bilthoven Netherlands NL-3720 BA ilthoven
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 11, volume: 64, anno: 1999,
pagine: 3861 - 3866
SICI:
0022-3263(19990528)64:11<3861:OOPUHT>2.0.ZU;2-M
Fonte:
ISI
Lingua:
ENG
Soggetto:
POLYCYCLIC AROMATIC-HYDROCARBONS; FLASH VACUUM PYROLYSIS; THERMAL INTERCONVERSIONS; COMBUSTION PRODUCTS; BENZENE-RING; IDENTIFICATION; REARRANGEMENT; FLAMES; PAH; DICYCLOPENTAPYRENES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
36
Recensione:
Indirizzi per estratti:
Indirizzo: Jenneskens, LW Univecht,cht, Debye Inst, Dept Phys Organ Chem, Padualaan 8, NL-3584 CH Utr Univ Utrecht Padualaan 8 Utrecht Netherlands NL-3584 CH tr
Citazione:
M. Sarobe et al., "Origin of pyrene under high temperature conditions in the gas phase. The pivotal role of phenanthrene", J ORG CHEM, 64(11), 1999, pp. 3861-3866

Abstract

4-Ethynylphenanthrene (15), and the latent precursors for 2-ethynyl- (18) and 3-ethynylphenanthrene (19), viz., 2-(1-chloroethenyl)- (16) and 3-(1-chloroethenyl)phenanthrene (17), respectively, have been subjected to flash vacuum thermolysis (FVT). Whereas at 800 degrees C 15 is quantitatively converted into pyrene (1), 16 and 17 only give 18 and 19, respectively. Both 18and 19 contain redundant ethynyl substituents, i.e., after ethynyl-ethylidene carbene equilibration neither five- nor six-membered ring formation canoccur by carbene C-H insertion. At T greater than or equal to 1000 degreesC 16 and 17 gave pyrolysates containing the same set of 11 (non)-alternantpolycyclic aromatic hydrocarbons (PAH), albeit in a different ratio. The different product ratio suggests that redundant ethynyl substituents migratealong the phenanthrene periphery presumably via transient cyclobuta-PAH intermediates toward positions suitable for either five- or six-membered ringformation by carbene C-H insertion. The results provide an explanation forthe ubiquitous formation of pyrene (1), acephenanthrylene (9), and fluoranthene (3) during (incomplete) combustion. Phenanthrene (2) appears to be a point of divergence in PAH growth by C-2 addition.

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Documento generato il 30/10/20 alle ore 07:19:29