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

doi:10.1016/j.tetlet.2012.11.068

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 journal › Article › peer-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 language	English (US)
Pages (from-to)	526-529
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2012.11.068
State	Published - Feb 6 2013
Externally published	Yes

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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10.1016/j.tetlet.2012.11.068

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

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.",

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

author = "Lidia Marin and Yuexing Zhang and Koen Robeyns and Beno{\^i}t Champagne and Peter Adriaensens and Laurence Lutsen and Dirk Vanderzande and David Bevk and Wouter Maes",

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 Sp{\'e}ciaux de Recherche of the Acad{\'e}mie 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. ",

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AU - Marin, Lidia

AU - Zhang, Yuexing

AU - Robeyns, Koen

AU - Champagne, Benoît

AU - Adriaensens, Peter

AU - Lutsen, Laurence

AU - Vanderzande, Dirk

AU - Bevk, David

AU - Maes, Wouter

N1 - 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.

PY - 2013/2/6

Y1 - 2013/2/6

N2 - 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.

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KW - Trivalent organophosphorus reagents

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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