Molecular belts. 2. Substrate-directed syntheses of belt-type and cage-type structures

Peter R. Ashton, Ulrich Girreser, Daniele Giuffrida, Franz H. Kohanke, John P. Mathias, Françisco M. Raymo, Francisco Raymo, J. Fraser Stoddart, David J. Williams

Research output: Contribution to journalArticle

99 Citations (Scopus)

Abstract

The trebly-diastereoselective synthesis and structural characterization of two macropolycyclic derivatives, which are based npon building blocks incorporating six-membered rings that are both [a,c]- and [a,d]-fused, have been achieved by a Diels-Alder oligomerization reaction sequence. The angular syn bisdienophile 3 has been used as a Diels-Alder building block with the bisdiene 12 in a trebly-diastereoselective synthesis of the angular macropolycyclic derivative 5. The incorporation of two diametrically-opposed [a,c]-fused units into the skeleton of 5 imposes a conical nature upon the cavity compared with the structures of macropolycyclic compounds such as the cyclacene derivatives 1 and 2. The construction of the angular macropolycyclic derivative 5 anticipates the use of the C trisdienophile 4, with the bisdiene 12, in the substrate-directed of a novel cage-like compound dubbed trinacrene 6. The structural characterization of both the angular macropolycyclic derivative 5 and trinacrene 6 has been achieved by high-field NMR spectroscopy and FABMS. In the operation of treble diastereoselectivity during each cycloaddition step dictates the structures of the products, underlining the utility of these stereoregular Diels-Alder oligomerizations to control the formations of molecular structures.

Original languageEnglish
Pages (from-to)5422-5429
Number of pages8
JournalJournal of the American Chemical Society
Volume115
Issue number13
StatePublished - Dec 1 1993
Externally publishedYes

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Cycloaddition Reaction
Derivatives
Substrates
Molecular Structure
Oligomerization
Skeleton
Magnetic Resonance Spectroscopy
Cycloaddition
Molecular structure
Nuclear magnetic resonance spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Ashton, P. R., Girreser, U., Giuffrida, D., Kohanke, F. H., Mathias, J. P., Raymo, F. M., ... Williams, D. J. (1993). Molecular belts. 2. Substrate-directed syntheses of belt-type and cage-type structures. Journal of the American Chemical Society, 115(13), 5422-5429.

Molecular belts. 2. Substrate-directed syntheses of belt-type and cage-type structures. / Ashton, Peter R.; Girreser, Ulrich; Giuffrida, Daniele; Kohanke, Franz H.; Mathias, John P.; Raymo, Françisco M.; Raymo, Francisco; Fraser Stoddart, J.; Williams, David J.

In: Journal of the American Chemical Society, Vol. 115, No. 13, 01.12.1993, p. 5422-5429.

Research output: Contribution to journalArticle

Ashton, PR, Girreser, U, Giuffrida, D, Kohanke, FH, Mathias, JP, Raymo, FM, Raymo, F, Fraser Stoddart, J & Williams, DJ 1993, 'Molecular belts. 2. Substrate-directed syntheses of belt-type and cage-type structures', Journal of the American Chemical Society, vol. 115, no. 13, pp. 5422-5429.
Ashton PR, Girreser U, Giuffrida D, Kohanke FH, Mathias JP, Raymo FM et al. Molecular belts. 2. Substrate-directed syntheses of belt-type and cage-type structures. Journal of the American Chemical Society. 1993 Dec 1;115(13):5422-5429.
Ashton, Peter R. ; Girreser, Ulrich ; Giuffrida, Daniele ; Kohanke, Franz H. ; Mathias, John P. ; Raymo, Françisco M. ; Raymo, Francisco ; Fraser Stoddart, J. ; Williams, David J. / Molecular belts. 2. Substrate-directed syntheses of belt-type and cage-type structures. In: Journal of the American Chemical Society. 1993 ; Vol. 115, No. 13. pp. 5422-5429.
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