Cyanuric Chloride

Probst, Donald A.; Hanson, Paul R.; Barda, David A.

doi:10.1002/047084289x.rn00320

Cited by 5 publications

(2 citation statements)

References 42 publications

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“…While this method offers significant advantages in terms of efficiency and cost compared to classical amide formation methods, the toxicity and hazards of TCT remain a concern (Figure 1a). [59] Chloro‐disubstituted triazines are safer reagents, [57,60,61] but require the use of a tertiary base, typically NMM ( N ‐methylmorpholine), which leads to the formation of an ammonium chloride intermediate (Figure 1b). This intermediate, known as DMTMM (4‐(4,6‐dimethoxy‐1,3,5‐triazin‐2‐yl)‐4‐methylmorpholinium chloride), is an effective coupling agent that can be used in pure water or with a co‐solvent [62,63] .…”

Section: Introductionmentioning

confidence: 99%

Catalytic and Sustainable Amide Bond Formation using a DABCO/Dichlorotriazine System

2023

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Amides are one of the most important functional groups in organic chemistry and play essential roles in both the pharmaceutical industry and life sciences. However, due to the natural reactivity of carboxylic acids and amines, their direct coupling is challenging and often leads to reactions that are not atom-economic and produce large amounts of nonrecoverable by-products. Despite the impressive number of coupling reagents available, sustainable methods for amide bond formation are still needed. To address this challenge, a new catalytic approach for the direct preparation of amides from carboxylic acids and amines is reported here. This method combines organocatalysis with a substoichiometric amount of activating agent under mild conditions (open air, room temperature, green solvents). This method was applied with good efficiency on a wide range of substrates, without epimerization of chiral stereocenters and on SPPS.

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Section: Introductionmentioning

confidence: 99%

Catalytic and Sustainable Amide Bond Formation using a DABCO/Dichlorotriazine System

2023

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“…The most common chemical reaction hereof is the substitution of the chlorine atom of the commercially available 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride) with nucleophiles [3]. Cyanuric chloride has been known since the early 1800, and has a similar reaction profile to acyl chlorides, rather than alkyl chlorides; since then, it has received great attention as a chemical reagent for different chemical reactions, as shown in Scheme 1 [4,5].…”

Section: Introductionmentioning

confidence: 99%

Insight into the Synthesis and Characterization of Organophosphorus-Based Bridged Triazine Compounds

et al. 2019

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In this article, we report the synthesis of 2,4,6-substituted s-triazine-based organophosphorus compounds via a two-step process, which enables their production in high yields, and with a high purity as solids. In the first step, a Michaelis–Arbuzov rearrangement of cyanuric chloride with triethyl phosphite afforded 2,4,6-trisdiethoxyphosphinyl-1,3,5-triazine (HEPT). Subsequently, the nucleophilic substitution reaction on the triazine carbon was achieved, owing to the electron-withdrawing ability of the phosphonate groups. This characteristic of HEPT facilitated its derivatization with bi-functional amines, producing novel P–C containing bridged triazine organophosphorus compounds. The molecular structures of all of the compounds were confirmed by NMR spectroscopy, CHN elemental analysis, and single crystal X-ray analysis. In the thermogravimetric analysis in an N2 environment, >33% char formation was observed for the bridged compounds. The chemical composition analysis of the char obtained under the oxidative thermal decomposition of the bridged compounds confirmed the presence of phosphorus- and nitrogen-enriched species, which indicate their function in the condensed phase. Comparatively, the detection of HPO and H–C≡P in the gas phase during the pyrolysis of the bridged compounds can act as a source for PO•, which is known for its gas phase flame inhibition reactions. The synergy of significant char formation and the generation of intermediates leading to PO• during pyrolysis makes these molecules promising flame-retardant additives.

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Preparation of poly(oxanorbornene) based single and double-folding polymers via nucleophilic aromatic substitution reaction

Alkan,

Temel,

Durmaz

et al. 2024

European Polymer Journal

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Cyanuric Chloride

Cited by 5 publications

References 42 publications

Catalytic and Sustainable Amide Bond Formation using a DABCO/Dichlorotriazine System

Catalytic and Sustainable Amide Bond Formation using a DABCO/Dichlorotriazine System

Insight into the Synthesis and Characterization of Organophosphorus-Based Bridged Triazine Compounds

Preparation of poly(oxanorbornene) based single and double-folding polymers via nucleophilic aromatic substitution reaction

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