TY - JOUR
T1 - The reaction of superoxide with cinnamyl bromide
T2 - The surprising formation of an ether and an epoxy acetal
AU - Frimer, Aryeh A.
AU - Strul, Gila
AU - Gilinsky-Sharon, Pessia
PY - 1995/5/29
Y1 - 1995/5/29
N2 - The reaction of O2-• ( KO2 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 O2-• in the presence of 4 yielding dibenzyl ether and epoxycinnamaldehyde dibenzyl acetal. When the reaction was repeated with CH3I, the corresponding epoxycinnamaldehyde dimethyl acetal was the major product.
AB - The reaction of O2-• ( KO2 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 O2-• in the presence of 4 yielding dibenzyl ether and epoxycinnamaldehyde dibenzyl acetal. When the reaction was repeated with CH3I, the corresponding epoxycinnamaldehyde dimethyl acetal was the major product.
UR - http://www.scopus.com/inward/record.url?scp=0029063352&partnerID=8YFLogxK
U2 - 10.1016/0040-4020(95)00274-c
DO - 10.1016/0040-4020(95)00274-c
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AN - SCOPUS:0029063352
SN - 0040-4020
VL - 51
SP - 6337
EP - 6342
JO - Tetrahedron
JF - Tetrahedron
IS - 22
ER -