45. “The Electronic Structure of Phenylene and Naphthylene Bicyclobutanes. Photoelectron spectroscopy and model calculations”
    Gleiter, R.; Gubernator, K.; Eckert-Maksić, M.; Spanget-Larsen, J.; Bianco, B.; Gandillon, G.; Burger, U.
    Helv. Chim. Acta 1981, 64, 1312-1321.

The photoelectron (PE.) spectra of 1,2,3-methenoindane (2), 1,2,3-metheno-2,3-dihydro-1H-cyclopenta [b]naphthalene (3) and 1,2,3-metheno-2,3-dihydro-1H-phenalene (4) are investigated. The PE. spectrum of 1,3-methano-2,3-dihydrophenalene (7) is reported and compared with that of 4. The experimental results are analyzed in terms of empirical correlation diagrams and the results of semiempirical MINDO/3 and CNDO/S calculations. The analysis indicates that the strong impact of the bicyclobutylene group on the spectroscopic properties of the aromatic π-systems in 2, 3 and 4 is due to hyperconjugative interactions involving bicyclobutane Walsh orbitals.

DOI : 10.1002/hlca.19810640508 

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