SYNTHESIS, CHARACTERIZATION, AND REACTION CHEMISTRY OF TERT-BUTYL HYPOFLUORITE

被引：11

作者：

APPELMAN, EH ^{[1
]}

FRENCH, D ^{[1
]}

MISHANI, E ^{[1
]}

ROZEN, S ^{[1
]}

机构：

[1] TEL AVIV UNIV,RAYMOND & BEVERLY SACKLER FAC EXACT SCI,SCH CHEM,IL-69978 TEL AVIV,ISRAEL

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 04期

关键词：

D O I：

10.1021/ja00057a022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

tert-Butyl hypofluorite ((CH3)3COF) can be synthesized by the low-temperature reaction of elemental fluorine with tert-butyl alcohol dissolved in propionitrile or acetonitrile. The isolated compound, which melts around -94-degrees-C and has an extrapolated boiling point of about +40-degrees-C, has been characterized by mass, NMR, and IR spectrometry. The F-19 NMR shift of +67 ppm lies between the corresponding shifts of HOF and CH3OF and implies a rather high O-F bond energy. Although sterically crowded, tert-butyl hypofluorite adds to olefins to form beta-fluoro-tert-butoxy compounds. Addition is mainly in an anti mode, and the regioselectivity corresponds to the action of a hitherto unknown tert-butoxylium electrophile. Also formed are adducts containing F and CH2CN, the latter deriving from the acetonitrile solvent.

引用

页码：1379 / 1382

页数：4

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