ISSN:
0947-3440
Keywords:
Ulfert E. Wiersum
;
Flash vacuum thermolysis
;
Rearrangements
;
Ring contractions
;
Ring expansion
;
1,2-C and 1,2-H shifts
;
Semiempirical calculations
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The thermal interconversion of the C16H10 cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAH) fluoranthene (1), acephenanthrylene (2) and aceanthrylene (3) has been studied using Flash Vacuum Thermolysis (FVT). In contrast to previously reported flow-pyrolysis results, which gave the unexpected thermodynamic stability order 1 〉 3 〉 2, FVT temperature-conversion data unequivocally show the expected order 1 〉 2 〉 3. These results are supported by independent FVT experiments with 9-ethynylphenanthrene (4), 9-ethynylanthracene (5) and 5-(anthryl-9′-methylene)-2,2-dimethyl-1,3-dioxan-4,6-dione (6), which are precursors for acephenanthrylene (2) and aceanthrylene (3), respectively. The interpretation of the FVT results is corroborated by semiempirical AM1 calculations of the C16H10 potential energy surface.
Additional Material:
5 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970624
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