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https://hdl.handle.net/2440/133327
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Type: | Journal article |
Title: | Discovery and computational rationalization of diminishing alternation in [n]dendralenes |
Author: | Saglam, M.F. Fallon, T. Paddon-Row, M.N. Sherburn, M.S. |
Citation: | Journal of the American Chemical Society, 2016; 138(3):1022-1032 |
Publisher: | American Chemical Society |
Issue Date: | 2016 |
ISSN: | 0002-7863 1520-5126 |
Statement of Responsibility: | Mehmet F. Saglam, Thomas Fallon, Michael N. Paddon-Row and Michael S. Sherburn |
Abstract: | The [n]dendralenes are a family of acyclic hydrocarbons which, by virtue of their ability to rapidly generate structural complexity, have attracted significant recent synthetic attention. [3]Dendralene through [8]dendralene have been previously prepared but no higher member of the family has been reported to date. Here, we describe the first chemical syntheses of the "higher" dendralenes, [9]dendralene through [12]dendralene. We also report a detailed investigation into the spectroscopic properties and chemical reactivity of the complete family of fundamental hydrocarbons, [3]dendralene to [12]dendralene. These studies reveal the first case of diminishing alternation in behavior in a series of related structures. We also report a comprehensive series of computational studies, which trace this dampening oscillatory effect in both spectroscopic measurements and chemical reactivity to conformational preferences. |
Keywords: | Alkenes |
Rights: | © 2015 American Chemical Society |
DOI: | 10.1021/jacs.5b11889 |
Grant ID: | ARC |
Published version: | http://dx.doi.org/10.1021/jacs.5b11889 |
Appears in Collections: | Physics publications |
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