Abstract
The hydrocarbon series represented by tricyclo[5.5.0.02,8]- dodecatetraene (11), tricyclo[5.3.0.02,8]deca-3,5,9-triene (12), and 9,10-dimethylenetricyclo[5.3.0.02,8]deca-3,5-diene (13) has been synthesized from dimethyl e-truxillate. Stepwise belting of a preformed all-trans 1,2,3,4-tetrasubstituted cyclobutane with proper differentiation of the 1,3- and 2,4-positions is crucial to successful twofold annulation. The response of these structurally unusual hydrocarbons to thermal and photochemical activation is described. Especially revealing are their photoelectron spectra. For 11, a substantial interaction exists between the orthogonal 1,3-diene systems via the central fourmembered ring. The level of “ring conjugation” far exceeds that found in any spiroconjugated molecule. The contrasting behavior of 12 and 13 is reported as well. Finally, the experimental data are compared with theoretical predictions.
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