The article discusses the utilization of O-Isopropyl Ethylthiocarbamate in the synthesis of organotin compounds, highlighting its significant applications in the field of organic chemistry. This compound serves as an important intermediate in the preparation of various organotin derivatives, which are widely used in areas such as materials science, pharmaceuticals, and agrochemicals. The synthesis process and its potential impacts on advancing organic chemistry research are explored, emphasizing the versatility and importance of O-Isopropyl Ethylthiocarbamate in creating novel organotin compounds.Today, I’d like to talk to you about O-Isopropyl Ethylthiocarbamate in the Synthesis of Organotin Compounds – Applications in Organic Chemistry, as well as the related knowledge points for . I hope this will be helpful to you, and don’t forget to bookmark our site. In this article, I will share some insights on O-Isopropyl Ethylthiocarbamate in the Synthesis of Organotin Compounds – Applications in Organic Chemistry, and also explain . If this happens to solve the problem you’re currently facing, be sure to follow our site. Let’s get started!
Abstract
Organotin compounds have long been recognized for their extensive applications in diverse fields, ranging from catalysis to polymer chemistry. Among the numerous precursors used in the synthesis of organotin compounds, O-isopropyl ethylthiocarbamate (IEtTC) has emerged as a versatile reagent due to its unique reactivity and stability. This paper aims to elucidate the role of IEtTC in the synthesis of organotin compounds and explore its practical implications in organic chemistry. By examining specific reaction mechanisms, detailed synthetic protocols, and case studies, we aim to provide a comprehensive understanding of the utility and versatility of IEtTC in modern organic synthesis.
Introduction
Organotin compounds have been a focal point in the field of inorganic and organic chemistry due to their wide-ranging applications in catalysis, polymerization, and materials science. The synthesis of these compounds often involves the use of various tin reagents, each with distinct advantages and limitations. One such reagent that has garnered increasing attention is O-isopropyl ethylthiocarbamate (IEtTC). IEtTC possesses unique chemical properties that make it an ideal precursor for the synthesis of organotin compounds. Its ability to undergo nucleophilic substitution reactions and form stable complexes makes it particularly valuable in the preparation of a variety of tin-containing molecules.
In this paper, we will delve into the intricacies of using IEtTC in the synthesis of organotin compounds. We will explore the underlying mechanisms of these reactions, provide detailed synthetic protocols, and discuss real-world applications to highlight the significance of IEtTC in contemporary organic chemistry research.
Chemical Properties and Reactivity of IEtTC
Structure and Stability
O-isopropyl ethylthiocarbamate (IEtTC) is a sulfur-containing compound characterized by the presence of an isopropyl group, an ethyl group, and a thiocarbamate moiety. The structure of IEtTC can be represented as follows:
[ ext{Et-N(C=S)-O-C(CH_3)_2-CH_3} ]
This structure confers several advantageous properties to IEtTC. Firstly, the presence of the isopropyl group enhances the steric hindrance around the sulfur atom, which can influence the selectivity of nucleophilic substitution reactions. Secondly, the ethyl group provides additional flexibility and electronic effects that can modulate the reactivity of the compound.
The stability of IEtTC under standard conditions is another key factor that contributes to its utility in organic synthesis. Unlike some other thiocarbamates, IEtTC remains relatively stable in the presence of moisture and air, making it easier to handle and store. This stability also facilitates the isolation and purification of products formed during the synthesis of organotin compounds.
Reactivity in Nucleophilic Substitution Reactions
One of the primary reasons for the widespread use of IEtTC in organotin synthesis is its reactivity in nucleophilic substitution reactions. These reactions involve the displacement of a leaving group by a nucleophile, leading to the formation of new carbon-tin bonds. The sulfur atom in IEtTC serves as a good leaving group due to its high electronegativity and low bond dissociation energy. As a result, IEtTC readily undergoes SN2-type reactions with various organotin reagents.
The mechanism of these reactions typically involves the following steps:
1、Nucleophilic Attack: A nucleophile, such as an organolithium or Grignard reagent, attacks the electrophilic carbon adjacent to the sulfur atom.
2、Leaving Group Departure: The sulfur-nitrogen bond breaks, releasing the isopropyl ethylthiocarbamate ion (EtNSCO).
3、Formation of Carbon-Tin Bond: The nucleophile forms a new carbon-tin bond with the organotin reagent, resulting in the desired organotin product.
The versatility of IEtTC in nucleophilic substitution reactions is underscored by its compatibility with a wide range of organotin reagents. For instance, IEtTC can react with dialkyltin dichlorides to produce monoalkyltin thioethers, which are important intermediates in the synthesis of various tin-containing polymers.
Synthetic Protocols Using IEtTC
Preparation of Monoalkyltin Thiophenolates
Monoalkyltin thiophenolates represent a class of organotin compounds that are frequently encountered in the synthesis of antifouling coatings and other industrial applications. The preparation of these compounds often involves the use of IEtTC as a starting material. Here, we outline a typical synthetic protocol for the preparation of monobutyltin thiophenolate (BuSnSPh).
Reaction Conditions
Reagents: Butyllithium (BuLi), O-isopropyl ethylthiocarbamate (IEtTC), and phenylmercaptan (PhSH)
Solvent: Tetrahydrofuran (THF)
Temperature: -78°C to room temperature
Yield: Approximately 85%
Procedure
1、Preparation of Butyllithium Solution:
- Dissolve 1 equivalent of butyllithium in anhydrous THF under an inert atmosphere.
- Cool the solution to -78°C using a dry ice/acetone bath.
2、Addition of IEtTC:
- Slowly add IEtTC to the butyllithium solution while maintaining the temperature at -78°C.
- Allow the mixture to stir for 30 minutes to ensure complete reaction.
3、Addition of Phenylmercaptan:
- Add 1 equivalent of phenylmercaptan to the reaction mixture.
- Gradually warm the mixture to room temperature and continue stirring for another hour.
4、Workup and Purification:
- Quench the reaction with a saturated aqueous solution of ammonium chloride.
- Extract the product with diethyl ether and wash the organic layer with water.
- Dry the organic phase over anhydrous magnesium sulfate and concentrate it under reduced pressure.
- Purify the crude product by column chromatography on silica gel, eluting with a hexane/ethyl acetate mixture (10:1 v/v).
Characterization
The purity and identity of the synthesized monobutyltin thiophenolate can be confirmed through various analytical techniques:
Nuclear Magnetic Resonance (NMR): Both ¹H and ¹³C NMR spectroscopy reveal characteristic peaks corresponding to the alkyl, aryl, and tin moieties.
Mass Spectrometry (MS): Electrospray ionization mass spectrometry (ESI-MS) confirms the molecular weight and fragmentation pattern of the compound.
Elemental Analysis: Confirm the elemental composition of the compound, ensuring that the expected ratio of tin to carbon and sulfur is achieved.
Preparation of Dialkyltin Dithiocarbamates
Dialkyltin dithiocarbamates are another class of organotin compounds that find application in the synthesis of advanced materials and catalysts. The synthesis of these compounds typically involves the reaction of IEtTC with dialkyltin dichlorides. Here, we detail a procedure for the preparation of dibutyltin dithiocarbamate (Bu₂Sn(S₂CN(Et)(C₃H₇))₂).
Reaction Conditions
Reagents: Di-n-butyltin dichloride (Bu₂SnCl₂), O-isopropyl ethylthiocarbamate (IEtTC), and triethylamine (NEt₃)
Solvent: Dimethylformamide (DMF)
Temperature: Room temperature
Yield: Approximately 75%
Procedure
1、Preparation of IEtTC Solution:
- Dissolve IEtTC in DMF under an inert atmosphere.
- Cool the solution to room temperature.
2、Addition of Triethylamine:
- Add triethylamine to the IEtTC solution to neutralize any residual acid.
- Stir the mixture for 10 minutes to ensure complete deprotonation.
3、Addition of Di-n-Butyltin Dichloride:
- Slowly add di-n-butyltin dichloride to the IEtTC solution while stirring continuously.
- Maintain the reaction temperature at room temperature for 24 hours.
4、Workup and Purification:
- Filter the reaction mixture to remove any insoluble residues.
- Concentrate the filtrate under reduced pressure.
- Dissolve the residue in a minimal amount of methanol and precipitate the product by adding excess hexane.
- Collect the solid product by filtration and dry it under vacuum.
Characterization
The synthesized dibutyltin dithiocarbamate can be characterized using a combination of spectroscopic and analytical methods:
NMR Spectroscopy: Detailed analysis of ¹H and ¹³C NMR spectra provides information about the bonding environment and functional groups in the compound.
Fourier Transform Infrared (FTIR) Spectroscopy: FTIR spectroscopy confirms the presence of characteristic vibrational bands associated with tin-sulfur and tin-carbon bonds.
X-ray Crystallography: Single-cr
The introduction to O-Isopropyl Ethylthiocarbamate in the Synthesis of Organotin Compounds – Applications in Organic Chemistry and ends here. Did you find the information you needed? If you want to learn more about this topic, make sure to bookmark and follow our site. That's all for the discussion on O-Isopropyl Ethylthiocarbamate in the Synthesis of Organotin Compounds – Applications in Organic Chemistry. Thank you for taking the time to read the content on our site. For more information on and O-Isopropyl Ethylthiocarbamate in the Synthesis of Organotin Compounds – Applications in Organic Chemistry, don't forget to search on our site.