Synthesis of selectively fluorinated cyclohexanes: the observation of phenonium rearrangements during deoxyfluorination reactions on cyclohexane rings with a vicinal phenyl substituent

Tanya Bykova; Nawaf Al-Maharik; Alexandra Martha Zoya Slawin; David O'Hagan

doi:10.1016/j.jfluchem.2015.08.003

Synthesis of selectively fluorinated cyclohexanes: the observation of phenonium rearrangements during deoxyfluorination reactions on cyclohexane rings with a vicinal phenyl substituent

Tanya Bykova, Nawaf Al-Maharik, Alexandra Martha Zoya Slawin, David O'Hagan

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

Abstract

A study focused on the synthesis of a derivative of all-cis phenyl-2,3,5,6-tetrafluorocyclohexane, incorporating a methyl group at the benzylic position, found that the fluorination reactions of diepoxide and diol precursors, were susceptible to rearrangement and unexpected products. The origin of these rearranged products can be rationalised by aryl migrations occurring via phenonium ion intermediates, in adventitious pathways occurring during deoxofluorination reactions with hydrogen fluoride reagents.

Original language	English
Journal	Journal of Fluorine Chemistry
Volume	In press
Early online date	11 Aug 2015
DOIs	https://doi.org/10.1016/j.jfluchem.2015.08.003
Publication status	Published - 2015

Keywords

Phenonium rearrangement
Fluoroaliphatics
Deoxofluorination reactions
Fluorocyclohexanes
All-cis tetrafluorocyclohexane motif

Access to Document

10.1016/j.jfluchem.2015.08.003

Slawin_2015_JFC_Synthesis_AM
Copyright © 2015 Elsevier Science B.V. All rights reserved. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1016/j.jfluchem.2015.08.003
Accepted author manuscript, 2.23 MB

CF2 Group: The CF2 group as a conformational tool in the olfactory receptor response
O'Hagan, D. (PI)
EPSRC
20/05/13 → 19/05/16
Project: Standard
Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation
Woollins, J. D. (PI), Ashbrook, S. E. (CoI), Morris, R. E. (CoI) & Slawin, A. M. Z. (CoI)
EPSRC
1/01/13 → 31/03/13
Project: Standard
Upgrade Small Equipment Base: Small items of research equipment at the University of St Andrews. Supporting a new generation of physical sciences research
Woollins, J. D. (PI)
EPSRC
1/11/12 → 31/03/13
Project: Standard

Synthesis of selectively fluorinated cyclohexanes: the observation of phenonium rearrangements during deoxyfluorination reactions on cyclohexane rings with a vicinal phenyl substituent (dataset)
Bykova, T. (Creator), Al-Maharik, N. (Creator), Slawin, A. M. Z. (Creator) & O'Hagan, D. (Creator), Cambridge Crystallographic Data Centre, 2015
https://dx.doi.org/10.5517/cc1j9dhq and 3 more links, https://dx.doi.org/10.5517/cc1j9djr, https://dx.doi.org/10.5517/cc1j9dks, https://dx.doi.org/10.5517/cc1j9dlt (show fewer)
Dataset

Cite this

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title = "Synthesis of selectively fluorinated cyclohexanes: the observation of phenonium rearrangements during deoxyfluorination reactions on cyclohexane rings with a vicinal phenyl substituent",

abstract = "A study focused on the synthesis of a derivative of all-cis phenyl-2,3,5,6-tetrafluorocyclohexane, incorporating a methyl group at the benzylic position, found that the fluorination reactions of diepoxide and diol precursors, were susceptible to rearrangement and unexpected products. The origin of these rearranged products can be rationalised by aryl migrations occurring via phenonium ion intermediates, in adventitious pathways occurring during deoxofluorination reactions with hydrogen fluoride reagents.",

keywords = "Phenonium rearrangement, Fluoroaliphatics, Deoxofluorination reactions, Fluorocyclohexanes, All-cis tetrafluorocyclohexane motif",

author = "Tanya Bykova and Nawaf Al-Maharik and Slawin, {Alexandra Martha Zoya} and David O'Hagan",

year = "2015",

doi = "10.1016/j.jfluchem.2015.08.003",

language = "English",

volume = "In press",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier",

}

Synthesis of selectively fluorinated cyclohexanes: the observation of phenonium rearrangements during deoxyfluorination reactions on cyclohexane rings with a vicinal phenyl substituent. / Bykova, Tanya; Al-Maharik, Nawaf; Slawin, Alexandra Martha Zoya et al.
In: Journal of Fluorine Chemistry, Vol. In press, 2015.

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

TY - JOUR

T1 - Synthesis of selectively fluorinated cyclohexanes

T2 - the observation of phenonium rearrangements during deoxyfluorination reactions on cyclohexane rings with a vicinal phenyl substituent

AU - Bykova, Tanya

AU - Al-Maharik, Nawaf

AU - Slawin, Alexandra Martha Zoya

AU - O'Hagan, David

PY - 2015

Y1 - 2015

N2 - A study focused on the synthesis of a derivative of all-cis phenyl-2,3,5,6-tetrafluorocyclohexane, incorporating a methyl group at the benzylic position, found that the fluorination reactions of diepoxide and diol precursors, were susceptible to rearrangement and unexpected products. The origin of these rearranged products can be rationalised by aryl migrations occurring via phenonium ion intermediates, in adventitious pathways occurring during deoxofluorination reactions with hydrogen fluoride reagents.

AB - A study focused on the synthesis of a derivative of all-cis phenyl-2,3,5,6-tetrafluorocyclohexane, incorporating a methyl group at the benzylic position, found that the fluorination reactions of diepoxide and diol precursors, were susceptible to rearrangement and unexpected products. The origin of these rearranged products can be rationalised by aryl migrations occurring via phenonium ion intermediates, in adventitious pathways occurring during deoxofluorination reactions with hydrogen fluoride reagents.

KW - Phenonium rearrangement

KW - Fluoroaliphatics

KW - Deoxofluorination reactions

KW - Fluorocyclohexanes

KW - All-cis tetrafluorocyclohexane motif

U2 - 10.1016/j.jfluchem.2015.08.003

DO - 10.1016/j.jfluchem.2015.08.003

M3 - Article

SN - 0022-1139

VL - In press

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

Synthesis of selectively fluorinated cyclohexanes: the observation of phenonium rearrangements during deoxyfluorination reactions on cyclohexane rings with a vicinal phenyl substituent

Abstract

Keywords

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Projects

CF2 Group: The CF2 group as a conformational tool in the olfactory receptor response

Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation

Upgrade Small Equipment Base: Small items of research equipment at the University of St Andrews. Supporting a new generation of physical sciences research

Datasets

Synthesis of selectively fluorinated cyclohexanes: the observation of phenonium rearrangements during deoxyfluorination reactions on cyclohexane rings with a vicinal phenyl substituent (dataset)

Cite this