Discreteness of π-conjugation of 1,6-methano[10]annulene by troponoid fusion at the 3,4-positions

Yanmei Zhang, Eri Hisano, Reina Ohta, Ryuta Miyatake, Yoshikazu Horino, Mitsunori Oda*, Shigeyasu Kuroda

*この論文の責任著者

研究成果: ジャーナルへの寄稿学術論文査読

5 被引用数 (Scopus)

抄録

The tropone-fused 1,6-methano[10]annulene 4 was synthesized from 3,4-bis(bromomethyl)-1,6-methano[10]annulene and the protonation of 4 provided the hydroxytropylium ion-fused annulene 5. 1H NMR spectra of 4 and 5 exhibited an unequal shielding effect on the bridge hydrogens from the resulted π ring system, suggesting the existence of the significant homoconjugative transannular interaction on the nonadjacent carbons at the bridge and the discreteness of π-conjugation of the annulene between two bonds at the C7-C8 and C11-C12 to localize the C8-11 dienyl and the remaining parts. The X-ray crystallographic structures of 4 and 5 show relatively short atomic distance between those bridge carbons, and clear bond alternation of the dienyl part and the bond convergence of the remaining part in these compounds, supporting the spectral properties.

本文言語英語
ページ(範囲)888-892
ページ数5
ジャーナルTetrahedron Letters
49
5
DOI
出版ステータス出版済み - 2008/01/28

ASJC Scopus 主題領域

  • 生化学
  • 創薬
  • 有機化学

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