Tetrahedron p. 6861 - 6872 (1997)
Update date:2022-08-11
Topics:
Redon, Martine
Janousek, Zdenek
Viehe, Heinz G.
The Diels-Alder reaction of 2-phenylthio-3,3,3-trifluoropropene 1 and its derivatives sulfoxide 2 and sulfone 3, respectively was carried out with cyclopentadiene, 2,3-dimethylbutadiene, butadiene and isoprene to give the [4+2] cycloadducts in good to excellent yields. The particular reactivity of 2-phenylsulfinyl-3,3,3-trifluoropropene 2 is revealed as an α,β-isomerisation via cycloaddition, sulfenic acid elimination, readdition followed by retro Diels-Alder.
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