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Peraryl-X-onium ions of nitrogen and oxygen


Lu, Mengsi; Allemann, Oliver; Xu, Jun; Linden, Anthony; Baldridge, Kim K; Siegel, Jay S (2019). Peraryl-X-onium ions of nitrogen and oxygen. Organic Chemistry Frontiers, 6(15):2640-2646.

Abstract

Peraryl-X-onium ions of nitrogen and oxygen constitute an underexploited class of organoionic species. Comparison of the syntheses of these onium salts by silyl-cation-promoted C-F activation and diazonium decomposition supports the idea that both methods share a common type of reactive intermediate. Onium ions with carboranyl counterions allowed X-ray crystallographic characterization of these salts. B97-D/Def2-TZVPP(chloroform) computational studies predicted the atropisomerism in oxonium salts analogous to that of substituted biaryls. Ion pairing of racemic atropisomeric oxonium and spirotetraarylammonium ions with enantiopure BINPHAT and BINOL allowed NMR spectral assignment of each diastereomer.

Abstract

Peraryl-X-onium ions of nitrogen and oxygen constitute an underexploited class of organoionic species. Comparison of the syntheses of these onium salts by silyl-cation-promoted C-F activation and diazonium decomposition supports the idea that both methods share a common type of reactive intermediate. Onium ions with carboranyl counterions allowed X-ray crystallographic characterization of these salts. B97-D/Def2-TZVPP(chloroform) computational studies predicted the atropisomerism in oxonium salts analogous to that of substituted biaryls. Ion pairing of racemic atropisomeric oxonium and spirotetraarylammonium ions with enantiopure BINPHAT and BINOL allowed NMR spectral assignment of each diastereomer.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Organic Chemistry
Language:English
Date:1 January 2019
Deposited On:17 Dec 2019 15:51
Last Modified:29 Jul 2020 11:56
Publisher:Royal Society of Chemistry
ISSN:2052-4110
OA Status:Closed
Publisher DOI:https://doi.org/10.1039/c9qo00633h

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