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Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

dc.contributor.authorMloston, Grzegorz
dc.contributor.authorGrzelak, Paulina
dc.contributor.authorMikina, Maciej
dc.contributor.authorLinden, Anthony
dc.contributor.authorHeimgartner, Heinz
dc.date.accessioned2015-09-28T11:21:58Z
dc.date.available2015-09-28T11:21:58Z
dc.date.issued2015-04-28
dc.identifier.issn1860-5397
dc.identifier.urihttp://hdl.handle.net/11089/11998
dc.description.abstractSelected hetaryl and aryl thioketones react with acetylenecarboxylates under thermal conditions in the presence of LiClO4 or, alternatively, under high-pressure conditions (5 kbar) at room temperature yielding thiopyran derivatives. The hetero-Diels–Alder reaction occurs in a chemo- and regioselective manner. The initially formed [4 + 2] cycloadducts rearrange via a 1,3-hydrogen shift sequence to give the final products. The latter were smoothly oxidized by treatment with mCPBA to the corresponding sulfones.pl_PL
dc.description.sponsorshipThe authors thank the National Science Center (Cracow, Poland) for generous financial support (Grant Maestro-3 (Dec- 2012/06/A/ST5/00219). Skilful performance of microanalyses by Ms Hanna Jatczak and Ms Agnieszka Cieślińska (University of Łódź) is gratefully acknowledgedpl_PL
dc.language.isoenpl_PL
dc.publisherBeilstein Beilstein-Institut zur Förderung der Chemischen Wissenschaftenpl_PL
dc.relation.ispartofseriesBeilstein Journal of Organic Chemistry;2015
dc.rightsUznanie autorstwa 3.0 Polska*
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/pl/*
dc.subjectdimethyl acetylenedicarboxylate (DMAD)pl_PL
dc.subjecthetero-Diels–Alder reactionspl_PL
dc.subjecthigh pressure reactions; methyl propiolatepl_PL
dc.subjectthioketonespl_PL
dc.subjectthiopyranspl_PL
dc.titleHetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophilespl_PL
dc.typeArticlepl_PL
dc.page.number576–582pl_PL
dc.contributor.authorAffiliationMlostoń Grzegorz, Department of Organic and Applied Chemistry, University of Łódźpl_PL
dc.contributor.authorAffiliationGrzelak Paulina, Department of Organic and Applied Chemistry, University of Łódźpl_PL
dc.contributor.authorAffiliationMikina Maciej, Center of Molecular and Macromolecular Studies PASpl_PL
dc.contributor.authorAffiliationLinden Anthony, Department of Chemistry, University of Zürich, Winterthurerstrassepl_PL
dc.contributor.authorAffiliationHeimgartner Heinz, Department of Chemistry, University of Zürich, Winterthurerstrassepl_PL
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dc.contributor.authorEmailgmloston@uni.lodz.plpl_PL
dc.contributor.authorEmailheinz.heimgartner@chem.uzh.chpl_PL
dc.identifier.doi10.3762/bjoc.11.63
dc.relation.volume11pl_PL


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