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Me CAAC=N- : A Cyclic (Alkyl)(Amino)Carbene Imino Ligand.

ABSTRACT: A cyclic (alkyl)(amino)carbene (CAAC) has been shown to react with a covalent azide similar to the Staudinger reaction. The reaction of Me CAAC with trimethylsilyl azide afforded the N-silylated 2-iminopyrrolidine (Me CAAC=NSiMe3 ), which was fully characterized. This compound undergoes hydrolysis to afford the 2-iminopyrrolidine and trimethylsiloxane which co-crystallize as a hydrogen-bonded adduct. The N-silylated 2-iminopyrrolidine was used to transfer the novel pyrrolidine-2-iminato ligand onto both main-group and transition-metal centers. The reaction of the tetrabromodiborane bis(dimethyl sulfide) adduct with two equivalents of Me CAAC=NSiMe3 afforded the disubstituted diborane. The reaction of Me CAAC=NSiMe3 with TiCl4 and CpTiCl3 afforded Me CAAC=NTiCl3 and Me CAAC=NTiCl2 Cp, respectively.

SUBMITTER: Goettel JT

PROVIDER: S-EPMC7027825 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Me CAAC=N- : A Cyclic (Alkyl)(Amino)Carbene Imino Ligand.

Goettel James T JT Gao Haopeng H Dotzauer Simon S Braunschweig Holger H

Chemistry (Weinheim an der Bergstrasse, Germany) 20200109 5

A cyclic (alkyl)(amino)carbene (CAAC) has been shown to react with a covalent azide similar to the Staudinger reaction. The reaction of Me CAAC with trimethylsilyl azide afforded the N-silylated 2-iminopyrrolidine (Me CAAC=NSiMe3 ), which was fully characterized. This compound undergoes hydrolysis to afford the 2-iminopyrrolidine and trimethylsiloxane which co-crystallize as a hydrogen-bonded adduct. The N-silylated 2-iminopyrrolidine was used to transfer the nov ...[more]

PMID: 31777982

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