1998
DOI: 10.1002/(sici)1099-0690(199805)1998:5<799::aid-ejoc799>3.0.co;2-g
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Matrix Isolation of 3,4-Benzocyclodeca-3,7,9-triene-1,5-diyne

Abstract: 3,4‐Benzocyclodeca‐3,7,9‐triene‐1,5‐diyne (3) has been synthesized from two different precursors and characterized by means of matrix‐isolation spectroscopy. Energies, structures and IR spectra of the product, the intermediate 9,10‐didehydroanthracene (4), and of the transition state of the Bergman cyclization 3 → 4 have been calculated at the B3LYP‐6‐31G* level of theory.

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Cited by 8 publications
(9 citation statements)
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“…No evidence for dehydroanthracene 6 was obtained from these experiments, which suggests that 6 does not survive the gas-phase pyrolyses. This is in agreement with estimations from LFP experiments 53 and DFT calculations 54 of a barrier for the ring-opening of about 12 kcal/mol, even less than that of p-benzyne 3 (Figure 3). Since the ring-opening is predicted to be slightly exothermic, the chance of generating 6 via gasphase pyrolysis is very low.…”
Section: Derivatives Of M-and P-benzynesupporting
confidence: 90%
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“…No evidence for dehydroanthracene 6 was obtained from these experiments, which suggests that 6 does not survive the gas-phase pyrolyses. This is in agreement with estimations from LFP experiments 53 and DFT calculations 54 of a barrier for the ring-opening of about 12 kcal/mol, even less than that of p-benzyne 3 (Figure 3). Since the ring-opening is predicted to be slightly exothermic, the chance of generating 6 via gasphase pyrolysis is very low.…”
Section: Derivatives Of M-and P-benzynesupporting
confidence: 90%
“…The fast transient was assigned as 6 , while the slow transient was assigned the structure of the ring-opened 3,4-benzocyclodeca-3,7,9-triene-1,5-diyne 5 (Scheme ). Since the UV data of 6 from the LFP experiments 53 were in disagreement with the earlier matrix spectra, the alternative thermal precursors 19 and 20 were studied in our laboratory, and in addition the matrix photochemistry of bisketene 17 was reinvestigated …”
Section: Derivatives Of M- and P-benzynementioning
confidence: 99%
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“…Auch durch Pyrolyse verschiedener Vorstufen wurde stets nur 58 erhalten (Schema ) 125. 126 Anhand der DFT‐Rechnungen und der LFP‐Resultate wurde die Barriere für die Ringöffnung von 59 auf 10–12 kcal mol −1 abgeschätzt, das Diin 58 ist um etwa 6–8 kcal mol −1 stabiler als Didehydroanthracen 59 125. 126…”
Section: Para‐didehydroaromaten Und Die Bergman‐cyclisierungunclassified