92806-35-4Relevant academic research and scientific papers
Aromatic Claisen Rearrangements of Benzyl Ketene Acetals: Conversion of Benzylic Alcohols to (ortho-Tolyl)acetates
Burns, Jed M.,Krenske, Elizabeth H.,McGeary, Ross P.
supporting information, p. 252 - 256 (2017/01/24)
Claisen rearrangements of benzyl vinyl ethers are much less facile than those of aliphatic allyl vinyl ethers, and their synthetic utility has remained relatively unexplored. A one-pot procedure is reported for the generation and Claisen rearrangement of benzyl vinyl ethers that contain an activating α-alkoxy substituent on the vinyl group. A [3,3]-sigmatropic mechanism was supported by trapping of the intermediate isotoluene in an intramolecular Alder–ene reaction.
CYCLISATION DE DIARYLALCANES EN MILIEU SUPERACIDE: SYNTHESE DE CETONES TRICYCLIQUES A METHYLE ANGULAIRE ET MECANISME DE LEUR ISOMERISATION
Berrier, C.,Jacquesy, J. C.,Gesson, J. P.,Renoux, A.
, p. 1983 - 1994 (2007/10/02)
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.
