TY - JOUR
T1 - The Chemistry of Methyl Hypofluorite
T2 - Its Reactions with Various Unsaturated Centers
AU - Rozen, Shlomo
AU - Mishani, Eyal
AU - Kol, Moshe
AU - Ben-David, Iris
PY - 1994/7/1
Y1 - 1994/7/1
N2 - Methyl hypofluorite was until recently grouped as a hypothetical member of those smallest organic molecules which had not been synthesized. Passing F2 through a solution of methanol in MeCN or PrCN resulted in its successful preparation. MeOF is an unique reagent, since it generates the novel electrophilic methoxylium moiety in contrast to the much more common methoxide group. This hypofluorite was reacted with several types of olefins including benzylic, cyclic, bicyclic, straight chain, and steroidal ones. In most cases the regioselectivity is very good, reflecting the unique polarization of the reagent: MeOδ+Fδ-. The stereoselectivity tends to be less emphasized, but usually anti addition is dominant.
AB - Methyl hypofluorite was until recently grouped as a hypothetical member of those smallest organic molecules which had not been synthesized. Passing F2 through a solution of methanol in MeCN or PrCN resulted in its successful preparation. MeOF is an unique reagent, since it generates the novel electrophilic methoxylium moiety in contrast to the much more common methoxide group. This hypofluorite was reacted with several types of olefins including benzylic, cyclic, bicyclic, straight chain, and steroidal ones. In most cases the regioselectivity is very good, reflecting the unique polarization of the reagent: MeOδ+Fδ-. The stereoselectivity tends to be less emphasized, but usually anti addition is dominant.
UR - http://www.scopus.com/inward/record.url?scp=0000705621&partnerID=8YFLogxK
U2 - 10.1021/jo00094a047
DO - 10.1021/jo00094a047
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AN - SCOPUS:0000705621
VL - 59
SP - 4281
EP - 4284
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 15
ER -