Stereoselective and quantitative [2+2] photodimerization of a symmetrical octafluoro stilbene in the solid state: Face-to-face stacking of the fluorinated rings in trans-1,2-bis(2,3,5,6-tetrafluorophenyl)ethylene

Michael A Sinnwell; Benjamin J Ingenthron; Ryan H Groeneman; Leonard R MacGillivray

doi:10.1016/j.jfluchem.2016.05.010

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Stereoselective and quantitative [2+2] photodimerization of a symmetrical octafluoro stilbene in the solid state: Face-to-face stacking of the fluorinated rings in trans-1,2-bis(2,3,5,6-tetrafluorophenyl)ethylene

Journal article

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Stereoselective and quantitative [2+2] photodimerization of a symmetrical octafluoro stilbene in the solid state: Face-to-face stacking of the fluorinated rings in trans-1,2-bis(2,3,5,6-tetrafluorophenyl)ethylene

Michael A Sinnwell, Benjamin J Ingenthron, Ryan H Groeneman and Leonard R MacGillivray

Journal of fluorine chemistry, Vol.188, pp.5-9

08/2016

DOI: 10.1016/j.jfluchem.2016.05.010

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Abstract

The symmetrical octafluoro stilbene undergoes a stereoselective and quantitative [2+2] photodimerization in the solid state. CH⋯F interactions and face-to-face stacking dominate the self-assembly of the alkene in the solid. The resulting cyclobutane possesses four polyfluoro phenyl groups in a rctt-configuration. [Display omitted] •Stereoselective and quantitative [2+2] photodimerization.•Solid-state synthesis of fluoroarene.•Polyfluorophenyl interactions. The symmetrical octafluoro stilbene trans-1,2-bis(2,3,5,6-tetrafluorophenyl)ethylene (1) undergoes a stereoselective and quantitative [2+2] photodimerization in the solid state. The olefin self-assembles via C-H⋯F and face-to-face interactions of the fluorinated phenyl rings into a geometry for a topochemical photodimerization. The crystal structure and stereochemistry of the photoproduct rctt-1,2,3,4-tetrakis(2,3,5,6-tetrafluorophenyl)cyclobutane (2) has been determined.

[2 + 2] photodimerization

Self-assembly

Supramolecular chemistry

Details

Title: Subtitle: Stereoselective and quantitative [2+2] photodimerization of a symmetrical octafluoro stilbene in the solid state: Face-to-face stacking of the fluorinated rings in trans-1,2-bis(2,3,5,6-tetrafluorophenyl)ethylene
Creators: Michael A Sinnwell - Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA
Benjamin J Ingenthron - Department of Biological Sciences, Webster University, St. Louis, MO 63119, USA
Ryan H Groeneman - Department of Biological Sciences, Webster University, St. Louis, MO 63119, USA
Leonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA
Resource Type: Journal article
Publication Details: Journal of fluorine chemistry, Vol.188, pp.5-9
Publisher: Elsevier B.V
DOI: 10.1016/j.jfluchem.2016.05.010
ISSN: 0022-1139
eISSN: 1873-3328
Language: English
Date published: 08/2016
Academic Unit: Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
Record Identifier: 9984216708502771

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