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2001 Fiscal Year Final Research Report Summary

Studies on the Through Space n_0 → π^* and n_0 → σ^* Interaction

Research Project

Project/Area Number 11672126
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionKyoto Pharmaceutical University

Principal Investigator

NISHIDE Kiyoharu  Kyoto Pharmaceutical University, Associate Professor, 薬学部, 助教授 (10237711)

Co-Investigator(Kenkyū-buntansha) NODE Manabu  Kyoto Pharmaceutical University, Professor, 薬学部, 教授 (60027076)
Project Period (FY) 1999 – 2000
KeywordsFluoro group / Cyano group / X-Ray Crystallographic Analysis / Through Space n_F → π^* Interaction / Stereoselective Protonation / Aliphatic Fluorocyanides / Diels-Alder Reaction / Nucleophile-Electrophile Interaction
Research Abstract

We have investigated novel through-space n → π^* interactions to provide a new idea for regulation of the conformation of acyclic alkane compounds having fluoro and cyano groups to have the lager dipole moment. The results are summarized as follows : 1) An intramolecular n_F → π^* through-space attractive interaction has been found in 4-fluoro-2- (4-hydroxy- and 4-methoxyphenyl) decanenitriles by means of X-ray crystallographic analyses, 2) The new interaction makes it possible to freeze the conformation of their alkyl chain to have the larger dipole moment, 3) A syn diastereoselective protonation has been demonstrated on 4-fluore-2- (4-methoxyphenyl) decanenitriles due to the new interaction forming a pseudo five-membered ring including F and C (CN), 4) The new intermolecular n_0 → π^* through-space attractive interaction has been suggested to be the major controlling factor of endo/exo stereoselectivity over the usual Alder's second-orbital interaction in a Diels-Alder reaction of allene-1,3-dicarboxylates and N-alkoxycarbonylpyrroles.
We believe that these new findings are significant for the organic chemistry basis.

  • Research Products

    (6 results)

All Other

All Publications (6 results)

  • [Publications] Kiyoharu Nishide et al.: "A Novel Intramolecular Through-Space Interaction between F and CN : A Strategy for the Conformational Control of an Acyclic System"Chem.Commun.. 2394-2395 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kiyoharu Nishide et al.: "A Novel Attractive interaction in the Diels-Alder Reaction of N-Protected Pyrroles with Allene-1,3-carboxylate"Tetrahedron Lett.. 42. 9237-9240 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Manabu Node et al.: "New Asymmetric Transformation of Optically Active Allene-1,3-dicarboxylate and Its Application to the Formal Synthesis of (-)-Epibatidine"Chem.Commun.. 2363-2364 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kiyoharu Nishide, Yuri Hagimoto, Hiroaki Hasegawa, Motoo Shiro, and Manabu Node: "A Novel Intramolecular Through-Space Interaction between F and CN: A Strategy for the Conformational Control of an Acyclic System"Chem. Commun.. (22). 2394-2395 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kiyoharu Nishide, Shogo Ichihashi, Hiroyuki Kimura, Takahiro Katoh, and Manabu Node: "A Novel Attractive Interaction in the Diels-Alder Reaction of TV-Protected Pyrroles with Allene-1,3 carboxylate"Tetrahedron Lett.. 42 (52). 9237-9240 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Manabu Node, Kiyoharu Nishide, Toshio Fujiwara, and Shogo Ichihashi: "New Asymmetric Transformation of Optically Active Allene-1,3-dicarboxylate and Its Application to the Formal Synthesis of (-)-Epibatidine"Chem. Commun.. (21). 2363-2364 (1998)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2003-09-17  

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