Isolation and characterization of methyl hypofluorite (CH3OF)
作者:Moshe Kol、Shlomo Rozen、Evan Appelman
DOI:10.1021/ja00007a043
日期:1991.3
Methyl hypofluorite (CH 3 OF) has been prepared by the reaction of elemental fluorine with methanol in acetonitrile or propionitrile at low temperature. It was removed from the reaction mixture in a stream of nitrogen and purified by fractional distillation. The compound is moderately long-lived, although the liquid has exploded upon rapid warming. The liquid compound has a freezing point of about
次氟酸甲酯 (CH 3 OF) 是通过元素氟与甲醇在乙腈或丙腈中在低温下反应制备的。在氮气流中将其从反应混合物中除去并通过分馏纯化。该化合物的寿命适中,尽管这种液体在快速升温时会发生爆炸。液体化合物的凝固点约为 -142°C,蒸气压测量表明正常沸点为 -32.6±0.9°C,蒸发焓为 23.37±0.26 kJ/mol。蒸气的红外光谱与分子与 CH 3 OH 和 CF 3 OF 同构。该化合物还通过质谱和 1 H、 19 F 和 13 C NMR 光谱进行了表征。
The Chemistry of Methyl Hypofluorite: Its Reactions with Various Unsaturated Centers
Methyl hypofluorite was until recently grouped as a hypothetical member of those smallest organic molecules which had not been synthesized. Passing F-2 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: MeO(delta+)F(delta-). The stereoselectivity tends to be less emphasized, but usually anti addition is dominant.
KOL, MOSHE;ROZEN, SHLOMO;APPELMAN, EVAN, J. AMER. CHEM. SOC., 113,(1991) N, C. 2648-2651
作者:KOL, MOSHE、ROZEN, SHLOMO、APPELMAN, EVAN
DOI:——
日期:——
BAKLOUTI A.; CHAABOUNI M. M., J. FLUOR. CHEM., 1981, 18, NO 1, 45-56