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1995 Fiscal Year Final Research Report Summary

Design of Bowl-shaped Molecules and Their Application to the Stabilization of Highly Reactive Species

Research Project

Project/Area Number 06453062
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 物質変換
Research InstitutionThe University of Tokyo

Principal Investigator

OKAZAKI Renji  The University of Tokyo, Graduate School of Science, Professor, 大学院・理学系研究科, 教授 (70011567)

Project Period (FY) 1994 – 1995
KeywordsMolecular cavity / Cyclophane / Calixarene / Sulfenic acid / Molecular mechanics calculation / X-ray crystallographic analysis / aromatic azide / nitrene
Research Abstract

In this study bowl-shaped molecules with calix [6] arene and cyclophane skeletons were designed and synthesized. First, the synthesis of some new bicyclic cyclophanes having some functional groups were carried out using an orcinol benzyl ether unit as a central bridge and a diphenylmethane unit as a peripheral ring. The structures of these cyclophanes were studied by NMR and X-ray crystallography to show that the diameter of their cavity is about 14@90. The thermolysis of a compound having a sulfoxide functionality in the cavity gave the first stable arenesulfenic acid. Second, bowl-shaped molecules having a calix [6] arene skeleton were synthesized using calix [6] arenes and 2,6-bis (bromomethyl) benzene derivatives with azide and t-butylthio substituents in the cavity and their structures were studied by NMR and X-ray crystallography. Here again, a stable arenesulfenic acid was synthesized by thermolysis of a sulfoxide. Both bromo and sulfenic acid derivatives were shown to have 1,2,3-alternate conformations. The photolysis of an azide derivative afforded unusual products derived from insertion of the intermediary nitrene into calixarene ring.

  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] R.Okazaki: "Synthesis and Reactions of Stable Arenesulfenic Acid Bearing Bowl-Shaped Macrobicyclic Cyclophane Skeletons" Phosphorus, Sulfur, and Silicon. 95/96. 353-354 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] R.Okazaki: "Synthesis of a Stable Arenesulfenic Acid Bearing a Bowl-Shaped Macrobicyclic Cyclophane Skeleton" Angew. Chem., Int. Ed. Eng.34. 1124-1126 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] R.Okazaki: "Abnormal Reaction of an Aryl Azide Confined in a Calix [6] arene Skeleton" J. Chem. Soc., Chem. Commun.1899-1900 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] R.Okazaki: "Synthesis of Novel Lantern-Shaped Molecules Based on Resorcin [4] arene and m-Terphenyl Units" Tetrahedron Lett.36. 7677-7680 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] R.Okazaki: "Synthesis and Structure of a Bridged Calix [6] arene with a Sulfenic Acid Functionality in the Cavity" J. Org. Chem.61(in press). (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] R.Okazaki: "Synthesis and Reactions of Stable Arenesulfenic Acid Bearing Bowl-Shaped Macrobicyclic Cyclophane Skeletons" Phosphorus, Sulfur, and Silicon. 95/96. 353-354 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R.Okazaki: "Synthesis of a Stable Arenesulfenic Acid Bearing a Bowl-Shaped Macrobicyclic Cyclophane Skeleton" Angew.Chem., Int.Ed.Eng.34. 1124-1126 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R.Okazaki: "Abnormal Reaction of an Aryl Azide Confined in a Calix [6] arene Skeleton" J.Chem.Soc., Chem.Commun.1899-1900 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R.Okazaki: "Synthesis of Novel Lantern-Shaped Molecules Based on Resorcin [4] arene and m-Terphenyl Units" Tetrahedron Lett.36. 7677-7680 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R.Okazaki: "Synthesis and Structure of a Bridged Calix [6] arene with a Sulfenic Acid Functionality in the Cavity" J.Org.Chem.61(in press). (1996)

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

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Published: 1997-03-04  

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