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| - Structure of an Unsymmetrical Isomer from the AttemptedSynthesis of 1,8-Dicyclooctatetraenylnaphthalene
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| - Attempted synthesis of 1,8-dicyclooctatetraenylnaphthalene (1) by the palladium(0)-catalyzedcoupling of 1,8-dibromonaphthalene with cyclooctatetraenyltrimethylstannane afforded a singleunsymmetrical isomer of 1 in 88% yield. Two-dimensional NMR methods and spectral synthesiswere employed to assign the structure of the isomer (2). AM1 geometry-optimized structures of 2and its isomers showed that the unexpected unsymmetrical structure of 2 results from theminimization of repulsive inter-ring H−H interactions. Compound 2 is postulated to arise via tandem[2 + 2] cycloaddition and 6π → 4π + 2σ electrocyclization reactions of 1.
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