Acenaphane derivatives from furan macrocycles

Franz H. Kohnke; Melchiorre F. Parisi; Françisco M. Raymo; Paul A. O'Neil; David J. Williams

doi:10.1016/S0040-4020(01)85377-1

Acenaphane derivatives from furan macrocycles

Franz H. Kohnke, Melchiorre F. Parisi, Françisco M. Raymo, Paul A. O'Neil, David J. Williams

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

12 Scopus citations

Abstract

The macrocycle 1 reacts with benzynes to give the Diels-Alder tetra-adduct 11 as a single isomer in good yields. Its mode of formation has now been investigated and its stereochemistry confirimed by X-ray crystallographic analysis. Benzynes react with 1 stepwise with high regio and facial selectivity. Only the mono-adduct 2 could be aromatised to the furanaphthaphane 17, and its conformational behaviour has been investigated by means of dynamic ¹H NMR spectroscopy and by single crystal X-ray analysis. The tetra-adduct 11 exhibits molecular recognition in the solid state selectively entrapping p-xylene when crystallised from a mixture of xylenes.

Original language	English (US)
Pages (from-to)	9113-9124
Number of pages	12
Journal	Tetrahedron
Volume	50
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4020(01)85377-1
State	Published - 1994
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Acenaphane derivatives from furan macrocycles",

abstract = "The macrocycle 1 reacts with benzynes to give the Diels-Alder tetra-adduct 11 as a single isomer in good yields. Its mode of formation has now been investigated and its stereochemistry confirimed by X-ray crystallographic analysis. Benzynes react with 1 stepwise with high regio and facial selectivity. Only the mono-adduct 2 could be aromatised to the furanaphthaphane 17, and its conformational behaviour has been investigated by means of dynamic 1H NMR spectroscopy and by single crystal X-ray analysis. The tetra-adduct 11 exhibits molecular recognition in the solid state selectively entrapping p-xylene when crystallised from a mixture of xylenes.",

author = "{H. Kohnke}, Franz and {F. Parisi}, Melchiorre and {M. Raymo}, Fran{\c c}isco and {A. O'Neil}, Paul and {J. Williams}, David",

year = "1994",

doi = "10.1016/S0040-4020(01)85377-1",

language = "English (US)",

volume = "50",

pages = "9113--9124",

journal = "Tetrahedron",

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T1 - Acenaphane derivatives from furan macrocycles

AU - H. Kohnke, Franz

AU - F. Parisi, Melchiorre

AU - M. Raymo, Françisco

AU - A. O'Neil, Paul

AU - J. Williams, David

PY - 1994

Y1 - 1994

N2 - The macrocycle 1 reacts with benzynes to give the Diels-Alder tetra-adduct 11 as a single isomer in good yields. Its mode of formation has now been investigated and its stereochemistry confirimed by X-ray crystallographic analysis. Benzynes react with 1 stepwise with high regio and facial selectivity. Only the mono-adduct 2 could be aromatised to the furanaphthaphane 17, and its conformational behaviour has been investigated by means of dynamic 1H NMR spectroscopy and by single crystal X-ray analysis. The tetra-adduct 11 exhibits molecular recognition in the solid state selectively entrapping p-xylene when crystallised from a mixture of xylenes.

AB - The macrocycle 1 reacts with benzynes to give the Diels-Alder tetra-adduct 11 as a single isomer in good yields. Its mode of formation has now been investigated and its stereochemistry confirimed by X-ray crystallographic analysis. Benzynes react with 1 stepwise with high regio and facial selectivity. Only the mono-adduct 2 could be aromatised to the furanaphthaphane 17, and its conformational behaviour has been investigated by means of dynamic 1H NMR spectroscopy and by single crystal X-ray analysis. The tetra-adduct 11 exhibits molecular recognition in the solid state selectively entrapping p-xylene when crystallised from a mixture of xylenes.

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Acenaphane derivatives from furan macrocycles

Abstract

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