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
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

Files in This Item:
File Description SizeFormat 
trivalent organophosphorus.pdf
  Restricted Access
495.13 kBAdobe PDFView/Open    Request a copy
Show full item record

SCOPUSTM   
Citations

5
checked on Sep 5, 2020

WEB OF SCIENCETM
Citations

5
checked on May 14, 2022

Page view(s)

54
checked on May 15, 2022

Download(s)

40
checked on May 15, 2022

Google ScholarTM

Check

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.