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

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

Research output: Contribution to journalArticle

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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Benzene
benzene
rings
synthesis
Isomers
isomers
trienes
X rays
alternations
x rays
Crystalline materials
Molecules
molecules

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Synthesis of bis(germacyclopropa)benzenes and structures of their annelated benzene rings. / Tajima, Tomoyuki; Sasamori, Takahiro; Takeda, Nobuhiro; Tokitoh, Norihiro; Yoshida, Ken; Nakahara, Masaru.

In: Organometallics, Vol. 25, No. 1, 02.01.2006, p. 230-235.

Research output: Contribution to journalArticle

Tajima, T, Sasamori, T, Takeda, N, Tokitoh, N, Yoshida, K & Nakahara, M 2006, 'Synthesis of bis(germacyclopropa)benzenes and structures of their annelated benzene rings', Organometallics, vol. 25, no. 1, pp. 230-235. https://doi.org/10.1021/om0507629
Tajima, Tomoyuki ; Sasamori, Takahiro ; Takeda, Nobuhiro ; Tokitoh, Norihiro ; Yoshida, Ken ; Nakahara, Masaru. / Synthesis of bis(germacyclopropa)benzenes and structures of their annelated benzene rings. In: Organometallics. 2006 ; Vol. 25, No. 1. pp. 230-235.
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