Journal article
Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols: Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies
Crystal growth & design, Vol.15(12), pp.5744-5748
12/02/2015
DOI: 10.1021/acs.cgd.5b00939
Abstract
Regiocontrolled head-to-head and head-to-tail [2 + 2] photodimerizations of (E)-methyl-3-(pyridin-3-yl)prop-2-enoate are achieved in the solid state using 4,6-di-X-res (where X = Cl, Br, I; res = resorcinol) as small-molecule templates. The components in each co-crystal form discrete, three-component supramolecular assemblies sustained by two O-H···N hydrogen bonds. Whereas the head-to-head photoproduct (rctt)-dimethyl-3,4-bis(pyridin-3-yl)cyclobutane-1,2-dicarboxylate forms using 4,6-di-X-res (X = Cl or Br), the head-to-tail regioisomer (rctt)-dimethyl-2,4-bis(pyridin-3-yl)cyclobutane-1,3-dicarboxylate forms using 4,6-di-I-res. The head-to-tail product is generated via unexpected embraced dimeric assemblies. The stereochemistry of the head-to-tail product is confirmed using single-crystal X-ray diffraction.
Details
- Title: Subtitle
- Regiocontrol of the [2 + 2] Photodimerization in the Solid State Using Isosteric Resorcinols: Head-to-Tail Cyclobutane Formation via Unexpected Embraced Assemblies
- Creators
- Devin P Ericson - Department of Biological Sciences, Webster University, St. Louis, Missouri 63119, United StatesZachary P Zurfluh-Cunningham - Department of Biological Sciences, Webster University, St. Louis, Missouri 63119, United StatesRyan H Groeneman - Department of Biological Sciences, Webster University, St. Louis, Missouri 63119, United StatesElizabeth Elacqua - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United StatesEric W Reinheimer - Department of Chemistry and Biochemistry, W. M. Keck Foundation Center for Molecular Structure, California State University San Marcos, San Marcos, California 92096, United StatesBruce C Noll - Bruker AXS Inc., 5465 East Cheryl Parkway, Madison, Wisconsin 53711, United StatesLeonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
- Resource Type
- Journal article
- Publication Details
- Crystal growth & design, Vol.15(12), pp.5744-5748
- DOI
- 10.1021/acs.cgd.5b00939
- ISSN
- 1528-7483
- eISSN
- 1528-7505
- Grant note
- name: Faculty Development Fund, Webster University; DOI: 10.13039/100000078, name: Division of Materials Research, award: DMR-1408834
- Language
- English
- Date published
- 12/02/2015
- Academic Unit
- Chemistry; Pharmaceutical Sciences and Experimental Therapeutics
- Record Identifier
- 9984217451102771
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