Synthesis and Elaboration of All-cis-1,2,4,5-Tetrafluoro-3Phenylcyclohexane: A Polar Cyclohexane Motif

被引：23

作者：

Durie, Alastair J. ^{[1
]}

Fujiwara, Tomoya ^{[1
,2
]}

Cormanich, Rodrigo ^{[1
]}

Buehl, Michael ^{[1
]}

Slawin, Alexandra M. Z. ^{[1
]}

O'Hagan, David ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

[2] Toyama Univ, Grad Sch Med & Pharmaceut Sci, Sugitani, Toyama 9300194, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

aromatic transformations; cyclohexane; fluorinations; organofluorine compounds; polar organic motifs; SPECTRUM DEOXOFLUORINATING AGENT; ENHANCED THERMAL-STABILITY; SPACE HYDROGEN-FLUORINE; BIS(2-METHOXYETHYL)AMINOSULFUR TRIFLUORIDE; ORGANOFLUORINE CHEMISTRY; MEDICINAL CHEMISTRY; BOND ACCEPTOR; DEOXYFLUORINATION; CONFORMATION; NITRATIONS;

D O I：

10.1002/chem.201400354

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereocontrolled synthesis of all-cis-1,2,4,5- tetrafluoro-3-phenylcyclohexane is developed as the first functionalised example of this polar cyclohexane motif. The dipolar nature of the ring, arising due to two 1,3-diaxial CF bonds, is revealed in the solid-state (X-ray) structure. The orthogonal conformation of the aryl and cyclohexyl rings in all-cis-1,2,4,5-tetrafluoro-3-phenylcyclohexane, and in an ortho-nitro derivative, result in intramolecular (1h)J(HF) and (2h)J(CF)NMR couplings relayed through hydrogen bonding. The aryl group of all-cis-1,2,4,5-tetrafluoro-3-phenylcyclohexane is elaborated in different ways to demonstrate the versatility of this compound for delivering the motif to a range of molecular building blocks.

引用

页码：6259 / 6263

页数：5

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