Issue 99, 2018
From the journal:

Chemical Communications

Unconventional ionic ring-deconstruction pathways of a three-membered heterocycle†

Jan Fassbender,a   Gregor Schnakenburg,a   Derek P. Gates, ORCID logo *b   Arturo Espinosa Ferao ORCID logo *c  and  Rainer Streubel ORCID logo *a  

* Corresponding authors

a Institut für Anorganische Chemie der Rheinischen Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
E-mail: r.streubel@uni-bonn.de

b Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, Canada
E-mail: dgates@chem.ubc.ca

c Departamento de Química Orgánica, Universidad de Murcia, Campus de Espinardo, 30100 Murcia, Spain
E-mail: artuesp@um.es

Abstract

Two different ionic deconstructions of a three-membered COP ring have been discovered. The first involves displacement of the C[double bond, length as m-dash]O unit (aldehyde elimination) induced by base whilst the second involves acid-initiated extrusion of the ring-carbon (2-methyl-2-butene). Insight into the latter deconstruction was obtained by quantum chemical calculations.

Graphical abstract: Unconventional ionic ring-deconstruction pathways of a three-membered heterocycle

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Article information

DOI
https://doi.org/10.1039/C8CC08713J
Article type
Communication
Submitted
31 Oct 2018
Accepted
20 Nov 2018
First published
28 Nov 2018

Chem. Commun., 2018,54, 14013-14016

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Unconventional ionic ring-deconstruction pathways of a three-membered heterocycle

J. Fassbender, G. Schnakenburg, D. P. Gates, A. Espinosa Ferao and R. Streubel, Chem. Commun., 2018, 54, 14013 DOI: 10.1039/C8CC08713J

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