Issue 38, 2012
From the journal:

Chemical Communications

Rearrangement from the heteroantiaromatic borole to the heteroaromatic azaborine motif†‡

Sunanda Biswas,a   Cäcilia Maichle-Mössmerb  and  Holger F. Bettinger*a  

* Corresponding authors

a Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany
E-mail: holger.bettinger@uni-tuebingen.de
Fax: +49 7071 29-5422
Tel: +49 7071 29-72072

b Institut für Anorganische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

Abstract

Treatment of 9-chloro-9-borafluorene with N,O-bis(trimethylsilyl)hydroxylamine results in 10-trimethylsilyloxy-9-aza-10-boraphenanthrene 6b. NMR spectroscopy shows that the expected antiaromatic 9-(trimethylsilyloxyamino)-9-borafluorene 5b rearranges to the formally aromatic phenanthrene 6b at room temperature.

Graphical abstract: Rearrangement from the heteroantiaromatic borole to the heteroaromatic azaborine motif

  • This article is part of the themed collection: Aromaticity
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Article information

DOI
https://doi.org/10.1039/C2CC30914A
Article type
Communication
Submitted
08 Feb 2012
Accepted
16 Mar 2012
First published
30 Mar 2012

Chem. Commun., 2012,48, 4564-4566

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Rearrangement from the heteroantiaromatic borole to the heteroaromatic azaborine motif

S. Biswas, C. Maichle-Mössmer and H. F. Bettinger, Chem. Commun., 2012, 48, 4564 DOI: 10.1039/C2CC30914A

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