The evolution of molecular belts and collars

Franz H. Kohnke; J. Fraser Stoddart

doi:10.1351/pac198961091581

The evolution of molecular belts and collars

Franz H. Kohnke, J. Fraser Stoddart

Chemistry

Research output: Contribution to journal › Article › peer-review

47 Scopus citations

Abstract

The Diels-Alder reaction has been employed to synthesise a hexaepoxyoctacosahydro[12]cyclacene derivative 6 in a highly efficient manner from the syn-isomer 1 of 1,4:5,8-diepoxy-1,4,5,8-tetrahydroanthracene and 2,3,5,6-tetramethylene-7-oxabicyclo[2.2.1]heptane 2. Each time a new cyclohexene ring is formed in the macropolycyclisation process, which utilises two molar equivalents of both the bisdienophile 1 and the bisdiene 2, the cycloadditions are trebly diastereoselective. A sequence of reactions on compound 6 involving (i) deoxygenation, (ii) dehydration, and (iii) partial hydrogenation have led to the isolation and characterisation of the D_6h symmetrical dodecahydro[12]cyclacene derivative 10 containing six benzene rings. The synthetic strategy is new and the macropolycyclic compounds, which can be prepared according to this kind of molecular’LEGO’, are novel.

Original language	English (US)
Pages (from-to)	1581-1586
Number of pages	6
Journal	Pure and Applied Chemistry
Volume	61
Issue number	9
DOIs	https://doi.org/10.1351/pac198961091581
State	Published - Jan 1 1989

Funding

We are deeply indebted to Dr Neil S. lsaacs (University of Reading) for his assistance in performing high pressure reactions, to Mr Peter R. Ashton (University of Sheffield) for helping to identify many new compounds in the first instance by fast atom bombardment mass spectrometry, and to Dr David J. Williams and Miss Alexandra M.Z. Slawin (Imperial College London) for their rapid solutions to many awkward X-ray crystal structures. Much of the experimental data, on which this article is based, was obtained because of their enthusiastic cooperation. We thank the Science and Engineering Research Council, the Ministry of Defence, and the Johnson Matthey Technology Centre in the United Kingdom, and the University of Messina in Italy for their generous financial support. One (J.F.S.) of us acknowledges the award of a Research Fellowship from the Leverhulme Trust.

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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10.1351/pac198961091581

Cite this

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title = "The evolution of molecular belts and collars",

abstract = "The Diels-Alder reaction has been employed to synthesise a hexaepoxyoctacosahydro[12]cyclacene derivative 6 in a highly efficient manner from the syn-isomer 1 of 1,4:5,8-diepoxy-1,4,5,8-tetrahydroanthracene and 2,3,5,6-tetramethylene-7-oxabicyclo[2.2.1]heptane 2. Each time a new cyclohexene ring is formed in the macropolycyclisation process, which utilises two molar equivalents of both the bisdienophile 1 and the bisdiene 2, the cycloadditions are trebly diastereoselective. A sequence of reactions on compound 6 involving (i) deoxygenation, (ii) dehydration, and (iii) partial hydrogenation have led to the isolation and characterisation of the D6h symmetrical dodecahydro[12]cyclacene derivative 10 containing six benzene rings. The synthetic strategy is new and the macropolycyclic compounds, which can be prepared according to this kind of molecular{\textquoteright}LEGO{\textquoteright}, are novel.",

author = "Kohnke, {Franz H.} and Stoddart, {J. Fraser}",

note = "Funding Information: We are deeply indebted to Dr Neil S. lsaacs (University of Reading) for his assistance in performing high pressure reactions, to Mr Peter R. Ashton (University of Sheffield) for helping to identify many new compounds in the first instance by fast atom bombardment mass spectrometry, and to Dr David J. Williams and Miss Alexandra M.Z. Slawin (Imperial College London) for their rapid solutions to many awkward X-ray crystal structures. Much of the experimental data, on which this article is based, was obtained because of their enthusiastic cooperation. We thank the Science and Engineering Research Council, the Ministry of Defence, and the Johnson Matthey Technology Centre in the United Kingdom, and the University of Messina in Italy for their generous financial support. One (J.F.S.) of us acknowledges the award of a Research Fellowship from the Leverhulme Trust.",

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N2 - The Diels-Alder reaction has been employed to synthesise a hexaepoxyoctacosahydro[12]cyclacene derivative 6 in a highly efficient manner from the syn-isomer 1 of 1,4:5,8-diepoxy-1,4,5,8-tetrahydroanthracene and 2,3,5,6-tetramethylene-7-oxabicyclo[2.2.1]heptane 2. Each time a new cyclohexene ring is formed in the macropolycyclisation process, which utilises two molar equivalents of both the bisdienophile 1 and the bisdiene 2, the cycloadditions are trebly diastereoselective. A sequence of reactions on compound 6 involving (i) deoxygenation, (ii) dehydration, and (iii) partial hydrogenation have led to the isolation and characterisation of the D6h symmetrical dodecahydro[12]cyclacene derivative 10 containing six benzene rings. The synthetic strategy is new and the macropolycyclic compounds, which can be prepared according to this kind of molecular’LEGO’, are novel.

AB - The Diels-Alder reaction has been employed to synthesise a hexaepoxyoctacosahydro[12]cyclacene derivative 6 in a highly efficient manner from the syn-isomer 1 of 1,4:5,8-diepoxy-1,4,5,8-tetrahydroanthracene and 2,3,5,6-tetramethylene-7-oxabicyclo[2.2.1]heptane 2. Each time a new cyclohexene ring is formed in the macropolycyclisation process, which utilises two molar equivalents of both the bisdienophile 1 and the bisdiene 2, the cycloadditions are trebly diastereoselective. A sequence of reactions on compound 6 involving (i) deoxygenation, (ii) dehydration, and (iii) partial hydrogenation have led to the isolation and characterisation of the D6h symmetrical dodecahydro[12]cyclacene derivative 10 containing six benzene rings. The synthetic strategy is new and the macropolycyclic compounds, which can be prepared according to this kind of molecular’LEGO’, are novel.

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The evolution of molecular belts and collars

Abstract

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