Allylic Rearrangements. XV. The Carbonation of Butenylmagnesium Bromide

In the course of independent investigations in these Laboratories, studies have been made of the products resulting from the carbonation of the Grignard reagent derived from crotyl and methylvinylcarbinyl bromides. At the University of California, Los Angeles, this work was carried out as part of an extensive program of research on the nature of the allylic Grignard reagent and its reactions with a variety of substances. The approach, therefore, was one which gave detailed attention to all of the products formed in the reaction. On the other hand, certain studies now in progress at Princeton University on the reactions of the isomeric olefinic acids R-CH=CH--CH_2CO_2H (I), R-CH-(CO_2H)-CH=CH_2 (II), led to an investigation of the carbonation of allylic Grignard reagents with particular attention being focused on the acidic components of the reaction mixture, since it appeared that a convenient method of the synthesis for at least one and perhaps both of the isomerides I and II would be available if the reaction proved successful