Issue 21, 2022
From the journal:

Chemical Communications

Tetracyclic silaheterocycle formed through a pericyclic reaction cascade including a two-fold intramolecular C–C bond activation†

Joschua Helmer,a   Olli J. Pakkanen,b   Chris Gendy, ORCID logo b   Alexander Hepp,a   Heikki M. Tuononen ORCID logo *b  and  Felicitas Lips ORCID logo *a  

* Corresponding authors

a Institut für Anorganische und Analtische Chemie, Corrensstraße 20-30, 48149 Münster, Germany
E-mail: lips@uni-muenster.de

b Department of Chemistry, NanoScience Centre, P.O. Box 35, FI-40014 University of Jyväskylä, Finland
E-mail: heikki.m.tuononen@jyu.fi

Abstract

Reductive debromination of the tribromoamidosilane 2 gave the tetracyclic silaheterocycle 3 through a unique reaction cascade involving unprecedented two-fold intramolecular cycloaddition by transient silylenes. Experimental and computational analyses of the reaction mechanism allowed the identification of the key intermediates that lead to the silaheterocycle 3 or, alternatively, to the cyclotrisilene 19.

Graphical abstract: Tetracyclic silaheterocycle formed through a pericyclic reaction cascade including a two-fold intramolecular C–C bond activation

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Article information

DOI
https://doi.org/10.1039/D2CC00298A
Article type
Communication
Submitted
16 Jan 2022
Accepted
07 Feb 2022
First published
07 Feb 2022
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2022,58, 3549-3552

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Tetracyclic silaheterocycle formed through a pericyclic reaction cascade including a two-fold intramolecular C–C bond activation

J. Helmer, O. J. Pakkanen, C. Gendy, A. Hepp, H. M. Tuononen and F. Lips, Chem. Commun., 2022, 58, 3549 DOI: 10.1039/D2CC00298A

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