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

L. Marin, P. Adriaensens, D. Vanderzande, D. Bevk, W. Maes, Y. Zhang, B. Champagne, K. Robeyns, L. Lutsen

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

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.
langue originaleAnglais
Pages (de - à)526-529
Nombre de pages4
journalTetrahedron Letters
Volume54
Numéro de publication6
Les DOIs
étatPublié - 6 févr. 2013

Empreinte digitale

phosphine
X ray analysis
Chemical shift
Nuclear magnetic resonance
X-Rays
Single crystals
Derivatives
Geometry
Experiments
triethyl phosphite

Citer ceci

Marin, L., Adriaensens, P., Vanderzande, D., Bevk, D., Maes, W., Zhang, Y., ... Lutsen, L. (2013). Trivalent organophosphorus reagent induced pinacol rearrangement of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one. Tetrahedron Letters, 54(6), 526-529. https://doi.org/10.1016/j.tetlet.2012.11.068
Marin, L. ; Adriaensens, P. ; Vanderzande, D. ; Bevk, D. ; Maes, W. ; Zhang, Y. ; Champagne, B. ; Robeyns, K. ; Lutsen, L. / Trivalent organophosphorus reagent induced pinacol rearrangement of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one. Dans: Tetrahedron Letters. 2013 ; Vol 54, Numéro 6. p. 526-529.
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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.",
author = "L. Marin and P. Adriaensens and D. Vanderzande and D. Bevk and W. Maes and Y. Zhang and B. Champagne and K. Robeyns and L. Lutsen",
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Marin, L, Adriaensens, P, Vanderzande, D, Bevk, D, Maes, W, Zhang, Y, Champagne, B, Robeyns, K & Lutsen, L 2013, 'Trivalent organophosphorus reagent induced pinacol rearrangement of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one', Tetrahedron Letters, VOL. 54, Numéro 6, p. 526-529. https://doi.org/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. / Marin, L.; Adriaensens, P.; Vanderzande, D.; Bevk, D.; Maes, W.; Zhang, Y.; Champagne, B.; Robeyns, K.; Lutsen, L.

Dans: Tetrahedron Letters, Vol 54, Numéro 6, 06.02.2013, p. 526-529.

Résultats de recherche: Contribution à un journal/une revueArticle

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T1 - Trivalent organophosphorus reagent induced pinacol rearrangement of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one

AU - Marin, L.

AU - Adriaensens, P.

AU - Vanderzande, D.

AU - Bevk, D.

AU - Maes, W.

AU - Zhang, Y.

AU - Champagne, B.

AU - Robeyns, K.

AU - Lutsen, L.

N1 - Copyright 2013 Elsevier B.V., All rights reserved.

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.

AB - 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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