The "Metallo"-Diels-Alder Reactions: Examining the Metalloid Behavior of Germanimines

Matthew J Evans; Mathew D Anker; Ahmed Mouchfiq; Matthias Lein; J Robin Fulton

doi:10.1002/chem.201905693

The "Metallo"-Diels-Alder Reactions: Examining the Metalloid Behavior of Germanimines

Chemistry. 2020 Feb 26;26(12):2606-2609. doi: 10.1002/chem.201905693. Epub 2020 Feb 21.

Authors

Matthew J Evans¹, Mathew D Anker¹, Ahmed Mouchfiq¹, Matthias Lein¹, J Robin Fulton¹

Affiliation

¹ School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, 6012, New Zealand.

PMID: 31863493
DOI: 10.1002/chem.201905693

Abstract

Addition of MesN₃ (Mes=2,4,6-Me₃ C₆ H₂ ) to germylene [(NON^tBu )Ge] (NON^tBu =O(SiMe₂ NtBu)₂ ) (1) gives germanimine, [(NON^tBu )Ge=NMes] (2). Compound 2 behaves as a metalloid, showing reactivity reminiscent of both transition metal-imido complexes, undergoing [2+2] addition with heterocumulenes and protic sources, as well as an activated diene, undergoing a [4+2] cycloaddition, or "metallo"-Diels-Alder, reaction. In the latter case, the diene includes the Ge=N bond and π-system of the Mes substituent, which is reactive towards dienophiles including benzaldehyde, benzophenone, styrene, and phenylacetylene.

Keywords: Diels-Alder; N ligands; germanium; imine; metalloid; multiple bonds.