Facile Formation of Dihydroacepentalenediide from centro-Substituted  Tribenzotriquinacenes with C-C Bond Cleavage

Rainer Haag; Dietmar Kuck; Xiao-Yong Fu; James M. Cook; Armin de Meijere

doi:10.1055/s-1994-22846

Synlett 1994; 1994(5): 340-342
DOI: 10.1055/s-1994-22846

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Facile Formation of Dihydroacepentalenediide from centro-Substituted Tribenzotriquinacenes with C-C Bond Cleavage

Rainer Haag^* , Dietmar Kuck, Xiao-Yong Fu, James M. Cook, Armin de Meijere

^*Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, D-37077 Göttingen, Germany

Abstract

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Tribenzodihydroacepentalenediide 5, a potential precursor for tribenzoacepentalene 6, can be prepared in good yields from the easily accessible centro-substituted tribenzotriquinacenes 7a-c by treatment with an excess of n-butyl lithium/potassium t-pentoxide in the presence of tetramethylethyIene diamine (TMEDA). The dieter 16 of tribenzodihydroacepentalene 15, thus obtained after hydrolysis of 5 in up to 85% yield from readily accessible 7a, undergoes [2+2]-cycloreversion at 220 °C, and 15 is efficiently trapped in [2+4]-cycloadditions with non-volatile dienes like tetracyclone and anthracene to give structurally interesting polycycles 17 and 18, respectively.

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