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

5 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

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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