Artikel,

Electron rich olefins. 2. Structure and electron transfer reactivity of the cyclic s/p-hyperconjugated carbosilane 3,3,6,6-tetrakis(trimethylsilyl)-1,4-cyclohexadiene

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Zeitschrift fuer Naturforschung, B: A Journal of Chemical Sciences, 43 (9): 1087--1093 (1988)

Zusammenfassung

Crystal and mol. structure anal. of the title compd. (I), a highly electron rich carbosilane, exhibits a shallow boat conformation for the cyclohexadiene ring which is shielded by 4 bulky Me3Si groups. Multiple hyperconjugative interaction occurs between the 2-nonjugated olefinic p systems and the 4 rather long (192 pm) C-Si s bonds which form an angle of about 34° with the assumed p axis. The HOMO destabilization caused by this unique structural arrangement explains the energetically facile formation and subsequent reactivity of the cation radical I+ which undergo oxidative desilylation to form the arom. 1,4-bis(trimethylsilyl)benzene precursor in the single electron transfer reaction with TCNE. [on SciFinder(R)]

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