Thallium in organic synthesis. 57. Reaction of chalcones and chalcone ketals with thallium (III) trinitrate

…, RA Conley, DK Johnson, A McKillop…

Index: Taylor, Edward C.; Conley, Richard A.; Johnson, David K.; McKillop, Alexander; Ford, Michael E. Journal of Organic Chemistry, 1980 , vol. 45, # 17 p. 3433 - 3436

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Citation Number: 16

Abstract

Treatment of chalcones (ArCH== CHCOAr') with thallium (II1) 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.