Journal article
Supramolecular Construction of an Aldehyde-Cyclobutane via the Solid State: Combining Reversible Imine Formation and Metal-Organic Self-Assembly
Journal of the American Chemical Society, Vol.139(25), pp.8452-8454
06/28/2017
DOI: 10.1021/jacs.7b04420
PMID: 28605202
Abstract
A combination of metal-organic self-assembly and reversible imine formation is used to achieve an organic synthesis via the solid state. Imine bond formation is employed to install a pyridyl to the alkene trans-cinnamaldehyde while Ag(I) ions are used in a second step to assemble the pyridyl-functionalized alkene into a geometry in the solid state for an intermolecular [2 + 2] photodimerization. The alkene undergoes the cycloaddition reaction via a 1D coordination polymer to generate a pyridyl-functionalized cyclobutane stereoselectively and in quantitative yield. Removal of the pyridyl group affords the aldehyde-functionalized cyclobutane α-truxilaldehyde.
Details
- Title: Subtitle
- Supramolecular Construction of an Aldehyde-Cyclobutane via the Solid State: Combining Reversible Imine Formation and Metal-Organic Self-Assembly
- Creators
- Shalisa M Oburn - Department of Chemistry, University of Iowa , Iowa City, Iowa 52245-1297, United StatesDale C Swenson - Department of Chemistry, University of Iowa , Iowa City, Iowa 52245-1297, United StatesS V Santhana Mariappan - Department of Chemistry, University of Iowa , Iowa City, Iowa 52245-1297, United StatesLeonard R MacGillivray - Department of Chemistry, University of Iowa , Iowa City, Iowa 52245-1297, United States
- Resource Type
- Journal article
- Publication Details
- Journal of the American Chemical Society, Vol.139(25), pp.8452-8454
- DOI
- 10.1021/jacs.7b04420
- PMID
- 28605202
- ISSN
- 0002-7863
- eISSN
- 1520-5126
- Grant note
- DOI: 10.13039/100000078, name: Division of Materials Research, award: DMR-1408834
- Language
- English
- Date published
- 06/28/2017
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
- Record Identifier
- 9984216689202771
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