Bisacetals of aromatic ring-annelated benzo[a,d]bis{bicyclo[4.4.1]undeca-3,8-diene-11-one}. [3.3] [3.3l]orthocyclophanes with triple-layered benzo/benzo/benzo- and naphtho/benzo/naphtho-system

Shuntaro Mataka, Yoshiharu Mitoma, Thies Thiemann, Tsuyoshi Sawada, Masahiko Taniguchi, Masaru Kobuchi, Masashi Tashiro

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

Tetraesters anti 9a,b and syn-9a,b, which have three aromatic rings, were prepared by the reaction of benzocycloheptenediester 7 with 1,2,4,5-tetrakis(bromomethyl)benzene. Subsequent hydrolysis and pyrolysis gave diketones anti-11a,b and syn-11a,b, which were acetalized to yield bisacetals anti-5a,b and syn-5a,b. X-Ray crystallographic analyses indicate a symmetric (twin-chair)/(twin-chair)- conformation of anti-5a,b, in which two naphtho or benzo rings sandwich one benzene ring. Anti-5a and anti-5b(9b)) are rigid structures. The protons of their central aromatic rings show an up-field shift, due to an anisotropic effect of the facing outer aromatic units. In contrast, syn-5a,b are flexible structures.' The UV-spectra of anti-5a,b show a long wavelength shift, as compared to syn-5a,b, suggesting a through-space interaction among the aromatic rings.

Original languageEnglish
Pages (from-to)3015-3026
Number of pages12
JournalTetrahedron
Volume53
Issue number9
DOIs
Publication statusPublished - Mar 3 1997
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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