Synthesis and Crystal Structure of a Novel Derivative of 8,8-Dicyanoheptafulvene

DOI

Bibliographic Information

Other Title
  • 新規な8,8-ジシアノヘプタフルベン誘導体の合成と結晶構造

Description

Reaction of dispiro[cyclohexane-1,1'-(1',7'-dihydrocyclopenta[f]azlenium-7',1"-cyclohexane] perchlorate with bromomalonitrile in the presence of pyridine in dichlromethane provided 4'-(dicycanomethylidene)dispiro[cyclohexane-1,1'-(1',4'.7'-trihydrocyclopenta[f]azlene-7',1"-cyclohexane],in 14% yield. Its solid state structure was elucidated by X-ray crystallographic analysis. In the lattice two independent molecules exist with slightly differentbond angles and lengths. The central seven-membered ring has a boat form with the average bendingangles of 29° at the bow and 10° at the stern. The average exocyclic C-C bouble bond is 1.385 Å long. These values are close to the means between those of the planar parent of 8,8-dicyanoheptafulvene and 8,8-dicyano-1,6-dimethylheptafulvene, respectively. Ab initio calculations of various 1,6-disubstituted 8,8-dicyanoheptafulvene derivatives predicts thatthe seve-membered ring of 8,8-dicyanoheptafulvenes can change their form in variation of their bending angles and the exocyclic double bond lengths, depending on their substituents.

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Details 詳細情報について

  • CRID
    1390001205555254784
  • NII Article ID
    130004644742
  • DOI
    10.11494/kisoyuki.16.0.2057.0
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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