THE REACTION OF SUPEROXIDE WITH CINNAMYL BROMIDE - THE SURPRISING FORMATION OF AN ETHER AND AN EPOXY ACETAL

Authors
FRIMER AA STRUL G GILINSKYSHARON P
Citation
Aa. Frimer et al., THE REACTION OF SUPEROXIDE WITH CINNAMYL BROMIDE - THE SURPRISING FORMATION OF AN ETHER AND AN EPOXY ACETAL, Tetrahedron, 51(22), 1995, pp. 6337-6342
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
22
Year of publication
1995
Pages
6337 - 6342
Database
ISI
SICI code
0040-4020(1995)51:22<6337:TROSWC>2.0.ZU;2-C
Abstract
The reaction of O-2(-.) (KO2/18-crown-6 in toluene) with cinnamyl brom ide yielded neither the expected cinnamyl peroxide nor its Kornblum-De LaMare 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 re acted with O-2(-.) in the presence of 4 yielding dibenzyl ether and ep oxycinnamaldehyde dibenzyl acetal. When the reaction was repeated with CH3I, the corresponding epoxycinnamaldehyde dimethyl acetal was the m ajor product.