Tetrahedron

Cyclisatioh de diarylalcanes en milieu superacide: synthese de cetones tricycliques a methyle angulaire et mecanisme de leur isomerisation

C Berrier, JC Jacquesy, JP Gessom, A Renoux

Index: Berrier, C.; Jacquesy, J. C.; Gesson, J. P.; Renoux, A. Tetrahedron, 1984 , vol. 40, # 11 p. 1983 - 1994

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Citation Number: 4

Abstract

Cyclisation of readily available diary1-1, 2 ethanes 1→ 4 proceeds in SbF5,-HF at 0° C to yield tricyclic phenanthrenones 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 diprotonated 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 ...