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Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/14773

Title: Trivalent organophosphorus reagent induced pinacol rearrangement of 4H-cyclopenta[2,1-b:3,4-b ']dithiophen-4-one
Authors: Marin, Lidia
Zhang, Yuexing
Robeyns, Koen
Champagne, Benoit
Adriaensens, Peter
Lutsen, Laurence
Vanderzande, Dirk
Bevk, David
Maes, Wouter
Issue Date: 2013
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Citation: TETRAHEDRON LETTERS, 54 (6), p. 526-529
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[2,1-6:3,4-b']dithiophen)-5-one was achieved by combined NMR experiments, theoretical chemical shift and geometry calculations, and single crystal X-ray analysis. (C) 2012 Elsevier Ltd. All rights reserved.
Notes: [Marin, Lidia; Adriaensens, Peter; Vanderzande, Dirk; Bevk, David; Maes, Wouter] Hasselt Univ, Inst Mat Res IMO IMOMEC, B-3590 Diepenbeek, Belgium. [Zhang, Yuexing; Champagne, Benoit] Univ Namur, Chim Theor Lab, B-5000 Namur, Belgium. [Robeyns, Koen] Catholic Univ Louvain, Inst Condensed Matter & Nanosci Mol Solids & Reac, B-1348 Louvain, Belgium. [Lutsen, Laurence; Vanderzande, Dirk; Bevk, David] IMEC, IMOMEC Ass Lab, B-3590 Diepenbeek, Belgium.
URI: http://hdl.handle.net/1942/14773
DOI: 10.1016/j.tetlet.2012.11.068
ISI #: 000314388300019
ISSN: 0040-4039
Category: A1
Type: Journal Contribution
Validation: ecoom, 2014
Appears in Collections: Research publications

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