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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 | Source: | 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. | Keywords: | Chemistry, Organic;4H-Cyclopenta[2,1-b:3,4-b ']dithiophene; Pinacol rearrangement; Trivalent organophosphorus reagents; Chemical shift calculations; X-ray diffraction | Document URI: | http://hdl.handle.net/1942/14773 | ISSN: | 0040-4039 | e-ISSN: | 1873-3581 | DOI: | 10.1016/j.tetlet.2012.11.068 | ISI #: | 000314388300019 | Category: | A1 | Type: | Journal Contribution | Validations: | ecoom 2014 |
Appears in Collections: | Research publications |
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