Tetrahedron p. 1983 - 1994 (1984)
Update date:2022-08-05
Topics:
Berrier, C.
Jacquesy, J. C.
Gesson, J. P.
Renoux, A.
Cyclisation of redily available diaryl-1,2 ethanes 1-4 proceeds in SbF5-HF at 0oC to yield tricyclic phenantrenones 5,6,7 and 11 bearing an angular methyl group.This process implies the electrophilic attack of the more basic aromatic ring, reacting through its disprotonated form (on the oxygen and the meta carbon atom) on the second aromatic ring.Isomerization of these primary products may be observed (to give ketones 8,9,10 from 3 and 12 from 4) and it has been demonstrated by the use of specifically deuterated 3d that it involves stereospecific 1,2 hydride (or deuteride) shifts, without exchange.
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