TY - JOUR
T1 - Trivalent organophosphorus reagent induced pinacol rearrangement of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one
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.
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.
KW - 4H-Cyclopenta[2,1-b:3,4-b′]dithiophene
KW - Chemical shift calculations
KW - Pinacol rearrangement
KW - Trivalent organophosphorus reagents
KW - X-ray diffraction
UR - http://www.scopus.com/inward/record.url?scp=84872040180&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2012.11.068
DO - 10.1016/j.tetlet.2012.11.068
M3 - Article
AN - SCOPUS:84872040180
SN - 0040-4039
VL - 54
SP - 526
EP - 529
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 6
ER -