Treatment of alpha-ethenyl-alpha-phenylbenzenemethanol with iodine and
silver acetate in either acetic acid or benzene gave 1,2-diphenyl-3-i
odo-1-propanone (6) in 85% yield. Ring enlargements involving similar
rearrangements were observed with a number of cyclic vinyl carbinols.
In some cases, mixtures of normal Prevost products and rearranged beta
-iodo ketones were obtained. The exact scope of this apparently novel
reaction remains to be elucidated. Treatment of the beta-iodo ketones
with DBU gave the corresponding alpha,beta-unsaturated ketones from wh
ich a number of amino ketones and amino alcohols were prepared by conj
ugate addition followed by reduction.