Chemistry of syn-o,o‘-dibenzene
A new and improved synthesis cis,syn-o,o‘-dibenzene 1 was developed to obtain 1 in larger amounts with improved purity. syn-Dibenzene 1 undergoes thermolysis to two molecules of benzene at a rate slower than that of the thermodynamically more stable anti-dibenzene 2. Kinetic analysis revealed that t...
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| Hauptverfasser: | , , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
11/29/2000
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| In: |
Journal of the American Chemical Society
Year: 2000, Jahrgang: 122, Heft: 49, Pages: 12098-12111 |
| ISSN: | 1520-5126 |
| DOI: | 10.1021/ja0023579 |
| Online-Zugang: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1021/ja0023579 Verlag, lizenzpflichtig, Volltext: https://pubs.acs.org/doi/10.1021/ja0023579 
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| Verfasserangaben: | Hong Gan, M. Glenn Horner, Bruce J. Hrnjez, Thomas A. McCormack, John L. King, Zbigniew Gasyna, Grace Chen, Rolf Gleiter, and Nien-chu C. Yang |
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| 520 | |a A new and improved synthesis cis,syn-o,o‘-dibenzene 1 was developed to obtain 1 in larger amounts with improved purity. syn-Dibenzene 1 undergoes thermolysis to two molecules of benzene at a rate slower than that of the thermodynamically more stable anti-dibenzene 2. Kinetic analysis revealed that the higher thermal stability of 1 is due to the higher heat of activation in thermolysis. Photoelectron spectroscopy of 1 showed that the through-bond interaction between the two cyclohexadiene units in o,o‘-dibenzenes is more important than their through-space interaction. A comparative study on the thermolyses of related syn-o,o‘-arene:benzene dimers suggests that thermolyses of syn-o,o‘-arene:benzene dimers proceed via their anti-isomers as an intermediate. syn-Dibenzene 1 also undergoes adiabatic photolysis to one molecule of excited benzene and one molecule of ground-state benzene in good efficiency. The mechanisms of these reactions are discussed. | ||
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