A New Strategy for the Synthesis of Organosilicon Compounds of Cyclopropane Derivatives
Saeed Gholizadeh A , Kazem D. Safa
A C and Nader Noroozi Pesyan B
+ Author Affiliations
- Author Affiliations
A Organosilicon Research Laboratory, Faculty of Chemistry, University of Tabriz, Tabriz 51666-14766, Iran.
B Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia 57159, Iran.
C Corresponding author. Email: dsafa@tabrizu.ac.ir
Australian Journal of Chemistry 74(4) 245-251 https://doi.org/10.1071/CH20203
Submitted: 23 June 2020 Accepted: 5 October 2020 Published: 3 November 2020
Abstract
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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