Thallium in Organic Synthesis. 57. Reaction of Chalcones and Chalcone Ketals with Thallium(III) Trinitrate

Article abstract of DOI:10.1021/jo01305a011

Treatment of chalcones (ArCH=CHCOAr') with thallium(III) trinitrate (TTN) in acidic methanol or in trimethyl orthoformate (TMOF) gives 3,3-dimethoxy-1,2-diarylpropan-1-ones (oxythallation, Ar rearrangement) and/or methyl 2,3-diaryl-3-methoxypropanoates (in situ ketal formation, oxythallation, Ar' rearrangement).The effect of substituents on Ar and Ar' on the ratio of the above rearrangement products has been examined.