ADDITION OF PHENOLS TO PERFLUOROVINYL ETHERS - PROTONATION AND HALOGENATION OF CARBANIONIC INTERMEDIATES

被引：39

作者：

FEIRING, AE

WONCHOBA, ER

机构：

[1] Du Pont Central Research & Development, Experimental Station, Wilmington, Delaware 19880-0328

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 26期

关键词：

D O I：

10.1021/jo00052a008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fluorinated ethers ArOCF2CFHORf are obtained in good yield by base-catalyzed addition of phenols to perfluoroalkyl vinyl ethers, CF2=CFORf (Rf = C3F7, C3F7OCF(CF3)CF2, CH3O2CCF2CF2OCF(CF3)CF2). Reaction of sodium phenoxides with fluorinated vinyl ethers and hexachloroethane affords chlorinated ethers ArOCF2CFClORf. Treatment of BrCF2CFBrOC3F, with sodium phenoxide in the presence of CF2=CFOC3F7 gives PhOCF2CFBrOC3F7 in high yield at room temperature, probably by an anionic chain mechanism. Sodium phenoxide reacts cleanly with CF2=CFOC3F7 in the absence of an electrophile to give a 1:1 cis-trans mixture of olefins PhOCF=CFOC3F7. NMR chemical shifts of the OCF2CFHORf group proton shows an unusually large solvent dependence.

引用

页码：7014 / 7017

页数：4

共 28 条

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