Synthesis and elaboration of All-cis-1,2,4,5-Tetrafluoro-3Phenylcyclohexane: a polar cyclohexane motif

Alastair J. Durie; Tomoya Fujiwara; Rodrigo Cormanich; Michael Buehl; Alexandra M. Z. Slawin; David O'Hagan

doi:10.1002/chem.201400354

Synthesis and elaboration of All-cis-1,2,4,5-Tetrafluoro-3Phenylcyclohexane: a polar cyclohexane motif

Alastair J. Durie, Tomoya Fujiwara, Rodrigo Cormanich, Michael Buehl, Alexandra M. Z. Slawin, David O'Hagan^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	6259-6263
Number of pages	5
Journal	Chemistry - A European Journal
Volume	20
Issue number	21
DOIs	https://doi.org/10.1002/chem.201400354
Publication status	Published - 19 May 2014

Keywords

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

Access to Document

10.1002/chem.201400354

Novel organofluorine motifs: Novel organofluorine motifs in the service of industry
O'Hagan, D. (PI)
EPSRC
1/03/14 → 28/02/17
Project: Standard
HorizonCF: EU ERC Advanced Grant - HorizonCF: New horizons in organo-fluorine chemistry
O'Hagan, D. (PI)
European Commission
1/01/10 → 31/12/14
Project: Standard

Cite this

@article{da6c21a17293495baf065adfcb9bd032,

title = "Synthesis and elaboration of All-cis-1,2,4,5-Tetrafluoro-3Phenylcyclohexane: a polar cyclohexane motif",

abstract = "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.",

keywords = "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",

author = "Durie, {Alastair J.} and Tomoya Fujiwara and Rodrigo Cormanich and Michael Buehl and Slawin, {Alexandra M. Z.} and David O'Hagan",

note = "This work was supported by funding from the EPSRC and ERC Advanced Investigator Grant (GO802567). ",

year = "2014",

month = may,

day = "19",

doi = "10.1002/chem.201400354",

language = "English",

volume = "20",

pages = "6259--6263",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley & Sons, Ltd",

number = "21",

}

TY - JOUR

T1 - Synthesis and elaboration of All-cis-1,2,4,5-Tetrafluoro-3Phenylcyclohexane

T2 - a polar cyclohexane motif

AU - Durie, Alastair J.

AU - Fujiwara, Tomoya

AU - Cormanich, Rodrigo

AU - Buehl, Michael

AU - Slawin, Alexandra M. Z.

AU - O'Hagan, David

N1 - This work was supported by funding from the EPSRC and ERC Advanced Investigator Grant (GO802567).

PY - 2014/5/19

Y1 - 2014/5/19

N2 - 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.

AB - 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.

KW - Aromatic transformations

KW - Cyclohexane

KW - Fluorinations

KW - Organofluorine compounds

KW - Polar organic motifs

KW - SPECTRUM DEOXOFLUORINATING AGENT

KW - ENHANCED THERMAL-STABILITY

KW - SPACE HYDROGEN-FLUORINE

KW - BIS(2-METHOXYETHYL)AMINOSULFUR TRIFLUORIDE

KW - ORGANOFLUORINE CHEMISTRY

KW - MEDICINAL CHEMISTRY

KW - BOND ACCEPTOR

KW - DEOXYFLUORINATION

KW - CONFORMATION

KW - NITRATIONS

U2 - 10.1002/chem.201400354

DO - 10.1002/chem.201400354

M3 - Article

SN - 0947-6539

VL - 20

SP - 6259

EP - 6263

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 21

ER -

Synthesis and elaboration of All-cis-1,2,4,5-Tetrafluoro-3Phenylcyclohexane: a polar cyclohexane motif

Abstract

Keywords

Access to Document

Fingerprint

Projects

Novel organofluorine motifs: Novel organofluorine motifs in the service of industry

HorizonCF: EU ERC Advanced Grant - HorizonCF: New horizons in organo-fluorine chemistry

Cite this