Volume 27, Issue 16
Preparative Organic Chemistry
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ChemInform Abstract: Liquid-Phase Photofluorination with Elemental Fluorine. Part 3. Synthesis of Perfluorocycloalkyl Ethers with/without a Chlorine Substituent.

T. ONO

T. ONO

Natl. Ind. Res. Inst. Nagoya, Kita, Nagoya 462, Japan

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K. YAMANOUCHI

K. YAMANOUCHI

Natl. Ind. Res. Inst. Nagoya, Kita, Nagoya 462, Japan

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R. E. FERNANDEZ

R. E. FERNANDEZ

Natl. Ind. Res. Inst. Nagoya, Kita, Nagoya 462, Japan

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K. V. JUN. SCHERER

K. V. JUN. SCHERER

Natl. Ind. Res. Inst. Nagoya, Kita, Nagoya 462, Japan

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First published: April 16, 1996

Abstract

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ChemInform Abstract

Liquid-phase photofluorination of compound (I) leads to the desired perfluorinated cyclohexylmethoxypropane (II), the degradation product ( III) and an unusual rearranged product (IV). The Cl-containing ethers with cyclic structures (VII) are also perfluorinated by this method to give the corresponding Cl-containing F-ethers. The retention of the chlorine atom and the ability to have a benzene substituent on the substrate, substituents which are not tolerated in the electrochemical fluorination, are beneficial features of this novel perfluorinating method.

chemical structure image

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