The reaction of superoxide with cinnamyl bromide: The surprising formation of an ether and an epoxy acetal

Abstract

The reaction of O 2 −• ( KO 2 18- crown-6 in toluene) with cinnamyl bromide yielded neither the expected cinnamyl peroxide nor its Kornblum-DeLaMare fragmentation products, cinnamaldehyde ( 4) and cinnamyl alcohol. Instead we observed the novel formation of dicinnamyl ether and 2,3-epoxycinnamylaldehyde dicinnamyl acetal (88% yield). Benzyl bromide reacted with O 2 −• in the presence of 4 yielding dibenzyl ether and epoxycinnamaldehyde dibenzyl acetal. When the reaction was repeated with CH 3I, the corresponding epoxycinnamaldehyde dimethyl acetal was the major product.