Trivalent organophosphorus reagent induced pinacol rearrangement of 4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one
(2013) Tetrahedron Letters — Vol. 54, n° 6, p. 526-529 (2013)
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- 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.
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Marin, L., Zhang, Y., Robeyns, K., Champagne, B., Adriaensens, P., Lutsen, L., Vanderzande, D., Bevk, D., & Maes, W. (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 (Original work published 2013)