Trivalent organophosphorus reagent induced pinacol rearrangement of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one

Lidia Marin, Yuexing Zhang, Koen Robeyns, Benoît Champagne, Peter Adriaensens, Laurence Lutsen, Dirk Vanderzande, David Bevk, Wouter Maes*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

In this Letter we report on the reaction of 4H-cyclopenta[2,1-b:3,4- b′]dithiophen-4-one with various trivalent organophosphorus derivatives, with an emphasis on the final products depending on the applied reagents. No reaction occurred upon treatment with either triphenyl- or tricyclohexylphosphine, whereas addition of triethyl phosphite or tri(n-butyl)phosphine resulted in pinacol rearrangement. Structure elucidation of the isolated 5H-spiro(benzo[1,2-b:6,5-b′]dithiophene-4,4′- cyclopenta[2,1-b:3,4-b′]dithiophen)-5-one was achieved by combined NMR experiments, theoretical chemical shift and geometry calculations, and single crystal X-ray analysis.

Original languageEnglish (US)
Pages (from-to)526-529
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number6
DOIs
StatePublished - Feb 6 2013

Bibliographical note

Funding Information:
We gratefully thank BELSPO in the frame of the IAP P6/27 and IAP 7/05 networks. Y. Z. acknowledges the financial support of the Fonds Spéciaux de Recherche of the Académie Universitaire Louvain, co-funded by the Marie Curie Actions of the European Commission (ADi/DB/986.2011). The calculations were performed on the Interuniversity Scientific Computing Facility (ISCF), for which we acknowledge financial support from the FRS-FRFC (Convention No. 2.4.617.07.F) and from the University of Namur.

Keywords

  • 4H-Cyclopenta[2,1-b:3,4-b′]dithiophene
  • Chemical shift calculations
  • Pinacol rearrangement
  • Trivalent organophosphorus reagents
  • X-ray diffraction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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