Related Experiment Video
Updated: Jun 4, 2025
![The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F54498.jpg&w=3840&q=50)
The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique
Published on: November 28, 2016
Experimental verification of halomethyl carbinol synthesis from carbonyl compounds using a TiCl4-Mg bimetallic
Olga Michalak1, Sylwia Żurawicka1, Marek Kubiszewski2
1Pharmacy, Cosmetic Chemistry and Biotechnology Research Group, Łukasiewicz Research Network-Industrial Chemistry Institute Rydygiera 8 01-793 Warsaw Poland olga.michalak@ichp.lukasiewicz.gov.pl +48 453 056 175.
Abstract:
A critical evaluation of the feasibility of a previously published method for synthesising halomethyl carbinols from carbonyl compounds and CH2Br2 or CH2Cl2 using a bimetallic TiCl4-Mg complex is presented. The synthesis of compounds lacking the -CH2- group in their structure was achieved by following the procedures proposed in the reference literature or by introducing modifications to selected process parameters. These compounds were not identified as expected β-halohydrins but as products of reductive dimerisation or subsequent pinacolic rearrangement of carbonyl substrates. This paper proposes a formation mechanism of vicinal 1,2-diols in the presence of a TiCl4-Mg system, supported by experimental data and theoretical DFT calculations (DFT/B3LYP).
More Related Videos
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Related Concept Videos
Multiple Halogenation of Methyl Ketones: Haloform Reaction
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
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...
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Base-Promoted α-Halogenation of Aldehydes and Ketones
Acid Halides to Alcohols: Grignard Reaction
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...