α‐Fluorinated Ethers, Thioethers, and Amines: Anomerically Biased Species

“…In this field of organosulfur chemistry, thioether moieties are essential fragments of many biologically active compounds (3,4). For example, α-fluorinated thioethers are valuable compounds for modern agrochemicals (5). Also, there is a US patent (6) that discloses some thio derivatives of haloalkylpolyenes and their biological, specifically fungicidal, activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (Thio)substituted -1,3-Butadienes and -Butenynes

Kaçmaz

2019

Journal of the Turkish Chemical Society Section A: Chemistry

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In this study, 2H-1,1,3,4,4-pentachloro-1,3-butadiene (1) was reacted with different thiols (2methyl-2-propanethiol 2a, benzyl mercaptan 2b, 4-tert-butylbenzenethiol 2c, 4-nitrothiophenol 2d) in ethanol in the presence of NaOH to afford mono-thio-substituted-1,3-butadienes and mono-and tris-thiosubstituted-1-buten-3-ynes. Among them, (4-tert-butylphenyl)(1,3,4,4-tetrachlorobuta-1,3dienyl)sulfane (4c) exhibited two isomers of mono products. Moreover, the reaction of compound (1) with 2-hydroxythiophenol (2e) in dimethylformamide in the presence of triethylamine took place the formation of OH-protected butadiene structure 2-((Z)-1,3,4,4-tetrachlorobuta-1,3-dienylthio)phenol (4e) and ringclosed butadiene structure (E)-2-(2,3,3-trichloroallylidene)benzo[d][1,3]oxathiole (6), together and with two isomers of each. Their structures identified on the basis of GC-MS(+EI) analysis with different retention times (RT). Characterization of the synthesized compounds was done using several methods, mass spectrometry (GC-MS(+EI)), 1 H-, 13 C-, APT-NMR, FTIR and elemental analysis.

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“…They initially degrade in the troposphere through hydrogen atom abstraction by relatively abundant hydroxyl radicals. The literature is replete with studies on HFCs [1], their atmospheric reactions, and reactions of their degradation products [2].…”

Section: Introductionmentioning

confidence: 99%

Hydrogen Abstraction from Fluorinated Ethyl Methyl Ether Systems by OH Radicals

White

Martell

2016

Advances in Physical Chemistry

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A systematic computational investigation of hydrogen abstraction by OH from the full series of fluorinated ethyl methyl ethers (EME) containing at least one H and one F, C2HnX5-nOCHmX3-m (n=0–5, m=0–3; and n=m=0 not allowed), including 147 reactants and 469 transition states, has been carried out, employing the MP2/6-31G(d) level of theory. Results for optimized geometries, including evidence of intramolecular hydrogen bonding in transition states, and barrier heights are presented. Trends pertaining to the number of fluorines substituted, key bond lengths, barrier heights, and key bond angles were found with good correlations and were investigated. An increase in the number of F increases the barrier height of the reaction. An increase in some parameters such as C–H length of TS, relative change in C–H from reactants to TS, ∠COC of reactants, ∠HOH in the TS, and relative change in ∠HOH between TS and free water bond angle also correlates with increased barrier height. An increase in other parameters like C–H length in the reactants and hydrogen bonding can decrease the barrier height.

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α‐Fluorinated Ethers, Thioethers, and Amines: Anomerically Biased Species

Abstract: Organic chemistry Z 0200 α-Fluorinated Ethers, Thioethers, and Amines: Anomerically Biased Species -[291 refs.]. -(LEROUX, F.; JESCHKE, P.; SCHLOSSER*, M.; Chem. Rev. (Washington, D. C.) 105 (2005) 3, 827-856; Proc. Res., Bayer CropSci. AG, D-40789 Monheim, Germany; Eng.) -Lindner 26-254

Cited by 16 publications

References 1 publication

Interaction of the Azole N‐Sodium Derivatives with Freon‐113: Synthesis of N‐(2,2‐dichlorotrifluoroethyl)azoles

Interaction of the Azole N‐Sodium Derivatives with Freon‐113: Synthesis of N‐(2,2‐dichlorotrifluoroethyl)azoles

Synthesis of (Thio)substituted -1,3-Butadienes and -Butenynes

Hydrogen Abstraction from Fluorinated Ethyl Methyl Ether Systems by OH Radicals

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