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Article: Stereoselectivity in the synthesis of polyacene derivatives by repetitive Diels-Alder reactions

TitleStereoselectivity in the synthesis of polyacene derivatives by repetitive Diels-Alder reactions
Authors
Ashton, Peter R.Brown, George R.Smith, Diane R.Stoddart, J. FraserWilliams, David J.
Issue Date1993
Citation
Tetrahedron Letters, 1993, v. 34, n. 51, p. 8337-8340 How to Cite?
DOI: http://dx.doi.org/10.1016/S0040-4039(00)61425-9
AbstractThe bisaryne generated from 1,4,5,8-tetramethyl- 2,3,6,7-tetrabromonaphthalene reacts with 2,5-dymethylfuran to give - through the intermediacy of the 1:1 adduct 1 - the 2:1 adducts 2, with the major isomer 2a, the one with the anti-configuration as revealed by X-ray crystallography and rationalised by molecular mechanics. Diels-Alder reactions of the anti-bisdienophile 2a with 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane proceed with complete treble diastereoselectivity to give only one 1:1 adduct 3 and a single 2:1 adduct 4. © 1993.
Persistent Identifierhttp://hdl.handle.net/10722/332365
ISSN
0040-4039
2023 Impact Factor: 1.5
2023 SCImago Journal Rankings: 0.323
ISI Accession Number ID
WOS:A1993MN26300040

 

DC FieldValueLanguage
dc.contributor.authorAshton, Peter R.-
dc.contributor.authorBrown, George R.-
dc.contributor.authorSmith, Diane R.-
dc.contributor.authorStoddart, J. Fraser-
dc.contributor.authorWilliams, David J.-
dc.date.accessioned2023-10-06T05:10:53Z-
dc.date.available2023-10-06T05:10:53Z-
dc.date.issued1993-
dc.identifier.citationTetrahedron Letters, 1993, v. 34, n. 51, p. 8337-8340-
dc.identifier.issn0040-4039-
dc.identifier.urihttp://hdl.handle.net/10722/332365-
dc.description.abstractThe bisaryne generated from 1,4,5,8-tetramethyl- 2,3,6,7-tetrabromonaphthalene reacts with 2,5-dymethylfuran to give - through the intermediacy of the 1:1 adduct 1 - the 2:1 adducts 2, with the major isomer 2a, the one with the anti-configuration as revealed by X-ray crystallography and rationalised by molecular mechanics. Diels-Alder reactions of the anti-bisdienophile 2a with 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane proceed with complete treble diastereoselectivity to give only one 1:1 adduct 3 and a single 2:1 adduct 4. © 1993.-
dc.languageeng-
dc.relation.ispartofTetrahedron Letters-
dc.titleStereoselectivity in the synthesis of polyacene derivatives by repetitive Diels-Alder reactions-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/S0040-4039(00)61425-9-
dc.identifier.scopuseid_2-s2.0-0027764308-
dc.identifier.volume34-
dc.identifier.issue51-
dc.identifier.spage8337-
dc.identifier.epage8340-
dc.identifier.isiWOS:A1993MN26300040-

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