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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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Bibliographic Details
Main Authors: Gan, Hong (Author) , Horner, M. Glenn (Author) , Hrnjez, Bruce J. (Author) , McCormack, Thomas A. (Author) , King, John L. (Author) , Gasyna, Zbigniew (Author) , Chen, Grace (Author) , Gleiter, Rolf (Author) , Yang, Nien-chu C. (Author)
Format: Article (Journal)
Language:English
Published: 11/29/2000
In: Journal of the American Chemical Society
Year: 2000, Volume: 122, Issue: 49, Pages: 12098-12111
ISSN:1520-5126
DOI:10.1021/ja0023579
Online Access: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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Author Notes: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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Summary: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.
Item Description:Gesehen am 03.11.2020
Physical Description:Online Resource
ISSN:1520-5126
DOI:10.1021/ja0023579

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