M. Newman, F. J. Evans
Feb 1, 1955
Citations
0
Influential Citations
35
Citations
Journal
Journal of the American Chemical Society
Abstract
Certain yield-diminishing side reactions of bromo esters in the Reformatsky reaction have been discussed previously. When ethyl cu-bromopropionate and ethyl a-bromoisobutyrate were used ethyl a-propionylpropionate and ethyl a-isobutyroylisobutyrate were formed in approximately 35 and 69% yields, respectively. When the above bromo esters were allowed to react with zinc alone in benzene the yields of keto esters were 39 and 6SY0, respectively. The present study was undertaken to see what effect the alkyl group in alkyl a-bromopropionates might have on the rate of self condensation and other side reactions. The reaction of methyl, ethyl, propyl, isopropyl, isobutyl, tbutyl and neopentyl a-bromopropionates with zinc in benzene-ether solvent in the presence and absence of benzophenone are herein described.