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Near Cancellation of Through Space and Through Bond Interaction in bicyclo[3.2.2]nona-6,8-diene

✍ Scribed by M. J. Goldstein; S. Natowsky; Edgar Heilbronner; V. Hornung

Publisher
John Wiley and Sons
Year
1973
Tongue
German
Weight
431 KB
Volume
56
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The photoelectron spectra of bicyclo[3.2.2]nonane and its five dehydrogenated analogues are reported. Analysis of the π‐bands reveals that the unsymmetrical diene 5 retains the ‘natural order’ of the π‐orbitals present in the lower homologues, i. e. the in‐phase below the out‐of‐phase combination of the basis π‐orbitals π~a~ and π~c~. The isomeric diene 4 is the first member of the symmetrical homologous series (I), which inverts this order, so that a~1~(π) (in phase!) lies above b~2~(π) (out‐of‐phase!).

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