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The “Metallo”‐Diels–Alder Reactions: Examining the Metalloid Behavior of Germanimines
Author(s) -
Evans Matthew J.,
Anker Mathew D.,
Mouchfiq Ahmed,
Lein Matthias,
Fulton J. Robin
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905693
Subject(s) - phenylacetylene , benzophenone , cycloaddition , reactivity (psychology) , chemistry , substituent , diene , diels–alder reaction , benzaldehyde , styrene , medicinal chemistry , transition metal , metalloid , metal , polymer chemistry , organic chemistry , catalysis , medicine , natural rubber , alternative medicine , polymer , pathology , copolymer
Addition of MesN 3 (Mes=2,4,6‐Me 3 C 6 H 2 ) to germylene [(NON t Bu )Ge] (NON t Bu =O(SiMe 2 N t Bu) 2 ) ( 1 ) gives germanimine, [(NON t Bu )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.