TY - JOUR
T1 - Olefin Epoxidation Using Elemental Fluorine
AU - Rozen, Shlomo
AU - Kol, Moshe
PY - 1990
Y1 - 1990
N2 - F2 reacts with water and CH3CN, apparently to produce the relatively stable complex HOF-CH3CN. This is probably the best known oxygen-transfer reagent and can epoxidize olefins quickly and efficiently. Various types of alkenes including aliphatic, benzylic, enones, dienones, maleates, and fumarates have been examined, and all react with the reagent to produce the corresponding mono- or diepoxides in good to excellent yields. This epoxidation is fully stereospecific, and the configuration of the starting olefin is fully retained in the resulting oxirane. In cases where exceptionally stable oxocarbocations can be formed as in 1,1-diphenylethene, the reaction produces vicinal glycols in good yields. Since the origin of the epoxides' oxygen is in the water, this method is very suitable for introducing the isotopes 170 and 180 into various molecules.
AB - F2 reacts with water and CH3CN, apparently to produce the relatively stable complex HOF-CH3CN. This is probably the best known oxygen-transfer reagent and can epoxidize olefins quickly and efficiently. Various types of alkenes including aliphatic, benzylic, enones, dienones, maleates, and fumarates have been examined, and all react with the reagent to produce the corresponding mono- or diepoxides in good to excellent yields. This epoxidation is fully stereospecific, and the configuration of the starting olefin is fully retained in the resulting oxirane. In cases where exceptionally stable oxocarbocations can be formed as in 1,1-diphenylethene, the reaction produces vicinal glycols in good yields. Since the origin of the epoxides' oxygen is in the water, this method is very suitable for introducing the isotopes 170 and 180 into various molecules.
UR - http://www.scopus.com/inward/record.url?scp=0000799155&partnerID=8YFLogxK
U2 - 10.1021/jo00304a031
DO - 10.1021/jo00304a031
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AN - SCOPUS:0000799155
SN - 0022-3263
VL - 55
SP - 5155
EP - 5159
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -