Synthesis of various cyclopropyl methyl bromide and its derivatives from ketones and/or aldehydes and some β-dicarbonyl compounds in the presence of BrCN and Et3N

The one-pot reaction of tetra-substituted cyclopropyl benzyl bromide with tris(trimethylsilyl)methyllithium (TsiLi) and carbon disulfide resulted in 3-(4-((((trimethylsilyl)ethynyl)thio)methyl)phenyl)cyclopropane-1,1,2,2-tetracarbonitrile (3) and 3-(4-((trimethylsilyl)methyl)phenyl)cyclopropane-1,2-dicarbonitrile (4) in excellent yield. The reaction in the absence of carbon disulfide yielded 3-(4-(2,2,2-tris(trimethylsilyl)ethyl)phenyl)cyclopropane-1,1,2,2-tetracarbonitrile (5) in excellent yield at 0°C to room temperature. All structures were characterised by IR, 1H NMR, and 13C NMR spectroscopies. The reaction mechanisms are discussed.

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A New Strategy for the Synthesis of Organosilicon Compounds of Cyclopropane Derivatives

Gholizadeh

Safa

Pesyan

2021

Aust. J. Chem.

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Magnetically reusable nanocatalysts in biginelli synthesis of dihydropyrimidinones (DHPMs)

Kazemi

2020

Synthetic Communications

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Synthesis of various cyclopropyl methyl bromide and its derivatives from ketones and/or aldehydes and some β-dicarbonyl compounds in the presence of BrCN and Et3N

Cited by 2 publications

References 19 publications

A New Strategy for the Synthesis of Organosilicon Compounds of Cyclopropane Derivatives

A New Strategy for the Synthesis of Organosilicon Compounds of Cyclopropane Derivatives

Magnetically reusable nanocatalysts in biginelli synthesis of dihydropyrimidinones (DHPMs)

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