FERROCENYL-SUBSTITUTED TETRAHYDROTHIOPHENES VIA FORMAL (3+2)-CYCLOADDITION REACTIONS OF FERROCENYL THIOKETONES WITH DONOR-ACCEPTOR CYCLOPROPANES

  1. Grzegorz MlostonORCID Logo,
  2. Mateusz KowalczykORCID Logo,
  3. André U. Augustin,
  4. Peter G. Jones and
  5. Daniel B. Werz

Submitting author affiliation: University of Lodz, Faculty of Chemistry, Lodz, Poland

Beilstein Arch. 2020, 202043. doi:10.3762/bxiv.2020.43.v1

Published 06 Apr 2020

  • Preprint

Abstract

Abstract

Ferrocenyl thioketones react with donor-acceptor cyclopropanes in dichloromethane at room temperature in the presence of catalytic amounts of Sc(OTf)3 yielding tetrahydrothiophene derivatives, products of formal (3+2)-cycloaddition reactions, in moderate to high yields. In all studied cases, dimethyl 2-arylcyclopropane dicarboxylates react with corresponding aryl ferrocenyl thioketones in a completely diastereoselective manner to form single products in which (C-2)-Ar and (C-5)-ferrocenyl groups are oriented in a cis-fashion. In contrast, the same cyclopropanes undergo reaction with alkyl ferrocenyl thioketones to form nearly equal amounts of both diastereoisomeric tetrahydrothiophenes. Low selectivity was also observed in the reaction of 2-phthalimide-derived cyclopropane with ferrocenyl phenyl thioketone.

Keywords: (3+2)-cycloaddition reactions; donor-acceptor cyclopropanes; ferrocenyl thioketones; sulfur heterocycles; tetrahydrothiophenes

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When a peer-reviewed version of this preprint is available in the Beilstein Journals, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Mloston, G.; Kowalczyk, M.; Augustin, A. U.; Jones, P. G.; Werz, D. B. Beilstein Arch. 2020, 202043. doi:10.3762/bxiv.2020.43.v1

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