Related Experiment Video
Updated: Aug 13, 2025

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
A germanimidoyl chloride: synthesis, characterization and reactivity
Abstract:
The first germanimidoyl chloride MsFluind-Ge(Cl)NMes (2, where MsFluind is a bulky hydrindacene skeleton) was synthesized through the reaction of MsFluind-GeCl (1) and mesityl azide (MesN3). In contrast, treatment of 1 with a less bulky azide ArN3 (Ar = 4-BuC6H4) produced a germatetrazole chloride MsFluind-Ge(Cl)N4Ar2 (3), and a salt [MsFluind-GeN4Ar2]+[BArF4]- (4; ArF = 3,5-(CF3)2C6H3) followed by chloride abstraction with NaBArF4, both bearing a five-membered GeN4 ring. Functionalization of 2 with Ar'Li (Ar' = 3,5-Bu2C6H3) or MeLi furnished a germanimine MsFluind-Ge(Ar')NMes (5) or an amide lithium salt MsFluind-Ge(Me)2-N(Mes)Li(thf) (6).
Related Concept Videos
Diazonium Group Substitution: –OH and –H
Acid Halides to Ketones: Gilman Reagent
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
Synthesis and Decomposition Reactions
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Alkyl Halides
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...

