Unexpected thermal decomposition of the “Alder carbene” (iPr2N)2C

Tim Schulz; Michael Leibold; Christian Färber; Martin Maurer; Timo Porsch; Max C. Holthausen; Ulrich Siemeling

doi:10.1039/C2CC34208A

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Unexpected thermal decomposition of the “Alder carbene” (iPr₂N)₂C†

Tim Schulz,^a Michael Leibold,^a Christian Färber,^a Martin Maurer,^a Timo Porsch,^b Max C. Holthausen^b and Ulrich Siemeling*^a

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* Corresponding authors

^a Institute of Chemistry, University of Kassel, Heinrich-Plett-Str. 40, D-34132 Kassel, Germany
E-mail: siemeling@uni-kassel.de

^b Institut für Anorganische und Analytische Chemie, Johann Wolfgang Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, D-60438 Frankfurt am Main, Germany

Abstract

The “Alder carbene” (iPr₂N)₂C undergoes a β-fragmentation in solution already at room temperature, affording propene and N,N,N′-triisopropylformamidine. This stands in sharp contrast to the indefinite stability previously claimed for this iconic compound.

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Article information

DOI: https://doi.org/10.1039/C2CC34208A
Article type: Communication
Submitted: 12 Jun 2012
Accepted: 17 Jul 2012
First published: 18 Jul 2012

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Chem. Commun., 2012,48, 9123-9125

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Unexpected thermal decomposition of the “Alder carbene” (iPr₂N)₂C

T. Schulz, M. Leibold, C. Färber, M. Maurer, T. Porsch, M. C. Holthausen and U. Siemeling, Chem. Commun., 2012, 48, 9123 DOI: 10.1039/C2CC34208A

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