Synthesis of bis(germacyclopropa)benzenes and structures of their annelated benzene rings

Tomoyuki Tajima, Takahiro Sasamori, Nobuhiro Takeda, Norihiro Tokitoh, Ken Yoshida, Masaru Nakahara

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33 Citations (Scopus)

Abstract

Extremely hindered bis(germacyclopropa)benzenes (3a,b; the IUPAC name is 4,8-digermatricyclo[5.1.0.03,5]octa-1,3(5),6-triene) were synthesized as stable crystalline compounds by the reaction of the corresponding dilithiogermane Tbt(Dip)GeLi2 (8; Tbt = 2,4,6- tris[bis(trimethylsilyl)methyl]phenyl, Dip = 2,6-diisopropylphenyl) with 1,2,4,5-tetrabromobenzene. The structures of the two stereoisomeric bis(germacyclopropa)benzenes (3a, cis isomer; 3b, trans isomer) were definitively determined by X-ray crystallographic analysis. The central benzene ring of 3a was found to be folded, in contrast to the planar benzene ring of 3b. The X-ray crystallographic analyses of 3a and 3b and the theoretical calculations for some model molecules revealed that the annelated benzene rings have no distinct bond alternation.

Original languageEnglish
Pages (from-to)230-235
Number of pages6
JournalOrganometallics
Volume25
Issue number1
DOIs
Publication statusPublished - Jan 2 2006
Externally publishedYes

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ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

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