Selectively fluorinated cyclohexane building blocks: derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane

Mohammed Salah Ayoup; David Bradford Cordes; Alexandra Martha Zoya Slawin; David O'Hagan

doi:10.3762/bjoc.11.287

Selectively fluorinated cyclohexane building blocks: derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane

Mohammed Salah Ayoup, David Bradford Cordes, Alexandra Martha Zoya Slawin, David O'Hagan^*

^*Corresponding author for this work

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

Abstract

Palladium catalysed carbonylation reactions using the meta- and para-iodo derivatives of all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane (4) are illustrated as the start point for a variety of functional group interconversions. The resultant benzaldehyde and benzoic acids offer novel building blocks for further derivatisation and facilitate the incorporation of the facially polarised all-cis-1,2,4,5-tetrafluorocyclohexane motif into more advanced molecular scaffolds.

Original language	English
Pages (from-to)	2671-2676
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	11
DOIs	https://doi.org/10.3762/bjoc.11.287
Publication status	Published - 21 Dec 2015

Keywords

Cyclohexane carbonylation
Fluorine containing building blocks: organofluorine chemistry

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10.3762/bjoc.11.287Licence: CC BY

O'Hagan_FluorinatedCyclohexane_BJoOC_CC
© 2015 Ayoup et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Final published version, 700 KBLicence: CC BY

Multivicinal fluorinated cyclohexanes: Multivicinal fluorinated cyclohexanes, a new structural motif in organic chemistry
O'Hagan, D. (PI)
EPSRC
31/07/10 → 1/08/10
Project: Standard
Synthesis and properties of novel sequen: Synthesis and properties of novel sequentially fluorinated motifs in organcic chemistry
O'Hagan, D. (PI)
EPSRC
24/03/08 → 23/03/11
Project: Standard

Selectively fluorinated cyclohexane building blocks: derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane (dataset)
Ayoup, M. S. (Creator), Cordes, D. B. (Creator), Slawin, A. M. Z. (Creator) & O'Hagan, D. (Creator), Cambridge Crystallographic Data Centre, 2015
https://dx.doi.org/10.5517/ccdc.csd.cc1k29sq and one more link, https://dx.doi.org/10.5517/ccdc.csd.cc1k29tr (show fewer)
Dataset

Cite this

@article{0ba43b62dabf462a9ed66a7cfe5c9c50,

title = "Selectively fluorinated cyclohexane building blocks: derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane",

abstract = "Palladium catalysed carbonylation reactions using the meta- and para-iodo derivatives of all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane (4) are illustrated as the start point for a variety of functional group interconversions. The resultant benzaldehyde and benzoic acids offer novel building blocks for further derivatisation and facilitate the incorporation of the facially polarised all-cis-1,2,4,5-tetrafluorocyclohexane motif into more advanced molecular scaffolds.",

keywords = "Cyclohexane carbonylation, Fluorine containing building blocks: organofluorine chemistry",

author = "Ayoup, {Mohammed Salah} and Cordes, {David Bradford} and Slawin, {Alexandra Martha Zoya} and David O'Hagan",

note = "MA thanks the Egyptian Government for a Scholarship under the Channel Scheme and we are grateful to the support of Professor L. Fathey of the University of Alexandria, Department of Chemistry, Egypt. DO'H thanks the Royal Society for a Wolfson Research Merit Award and we also thank the EPSRC Mass Spectrometry Service at Swansea University, UK for analyses.",

year = "2015",

month = dec,

day = "21",

doi = "10.3762/bjoc.11.287",

language = "English",

volume = "11",

pages = "2671--2676",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

TY - JOUR

T1 - Selectively fluorinated cyclohexane building blocks

T2 - derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane

AU - Ayoup, Mohammed Salah

AU - Cordes, David Bradford

AU - Slawin, Alexandra Martha Zoya

AU - O'Hagan, David

N1 - MA thanks the Egyptian Government for a Scholarship under the Channel Scheme and we are grateful to the support of Professor L. Fathey of the University of Alexandria, Department of Chemistry, Egypt. DO'H thanks the Royal Society for a Wolfson Research Merit Award and we also thank the EPSRC Mass Spectrometry Service at Swansea University, UK for analyses.

PY - 2015/12/21

Y1 - 2015/12/21

N2 - Palladium catalysed carbonylation reactions using the meta- and para-iodo derivatives of all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane (4) are illustrated as the start point for a variety of functional group interconversions. The resultant benzaldehyde and benzoic acids offer novel building blocks for further derivatisation and facilitate the incorporation of the facially polarised all-cis-1,2,4,5-tetrafluorocyclohexane motif into more advanced molecular scaffolds.

AB - Palladium catalysed carbonylation reactions using the meta- and para-iodo derivatives of all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane (4) are illustrated as the start point for a variety of functional group interconversions. The resultant benzaldehyde and benzoic acids offer novel building blocks for further derivatisation and facilitate the incorporation of the facially polarised all-cis-1,2,4,5-tetrafluorocyclohexane motif into more advanced molecular scaffolds.

KW - Cyclohexane carbonylation

KW - Fluorine containing building blocks: organofluorine chemistry

U2 - 10.3762/bjoc.11.287

DO - 10.3762/bjoc.11.287

M3 - Article

AN - SCOPUS:84961859368

SN - 1860-5397

VL - 11

SP - 2671

EP - 2676

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Selectively fluorinated cyclohexane building blocks: derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane

Abstract

Keywords

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Projects

Multivicinal fluorinated cyclohexanes: Multivicinal fluorinated cyclohexanes, a new structural motif in organic chemistry

Synthesis and properties of novel sequen: Synthesis and properties of novel sequentially fluorinated motifs in organcic chemistry

Datasets

Selectively fluorinated cyclohexane building blocks: derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane (dataset)

Cite this