Issue 15, 2019

Peraryl-X-onium ions of nitrogen and oxygen

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.

Graphical abstract: Peraryl-X-onium ions of nitrogen and oxygen

Supplementary files

Article information

Article type
Research Article
Submitted
13 May 2019
Accepted
04 Jun 2019
First published
12 Jun 2019

Org. Chem. Front., 2019,6, 2640-2646

Peraryl-X-onium ions of nitrogen and oxygen

M. Lu, O. Allemann, J. Xu, A. Linden, K. K. Baldridge and J. S. Siegel, Org. Chem. Front., 2019, 6, 2640 DOI: 10.1039/C9QO00633H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements