Reactions of 2-Halogen Ethers. I. The Action of Magnesium on Alkyl 2-Bromo-ethyl Ethers

Tallman, Ralph C.

doi:10.1021/ja01316a038

Cited by 24 publications

(3 citation statements)

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“…Elimination can proceed through a syn or an anti mechanism depending on the presence or absence of a Lewis acid. Another synthetic pathway would employ the use of an alkoxyethylorganometallic species (such as organomagnesium or organolithium species) reacting with a borate, but unfortunately, such organometallic species are not stable and tend to decompose rapidly …”

Section: Introductionmentioning

confidence: 99%

Suzuki–Miyaura Cross-Coupling of Potassium Alkoxyethyltrifluoroborates: Access to Aryl/Heteroarylethyloxy Motifs

et al. 2012

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The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-coupling strategy based on the exceptional properties of organotrifluoroborates has been developed, and the method allows an easy and efficient installation of this unit on a broad range of aryl and heteroaryl bromides.

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Section: Introductionmentioning

confidence: 99%

Suzuki–Miyaura Cross-Coupling of Potassium Alkoxyethyltrifluoroborates: Access to Aryl/Heteroarylethyloxy Motifs

et al. 2012

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“…Cooper and Partridge report a value of 949.9 kg·m –3 , while Ashburn reports a value of 889.3 kg·m –3 . In addition, there are several density measurements reported at lower temperatures: 892.7, 900.3, and 815.4 kg·m –3 , at 293.15 K and 892.6 kg·m –3 at 288.15 K . These reported density values differ vastly, where the value of 900.3 kg·m –3 is the most recent reported value (1973) of these and agrees closest with the respective data entry of 907.4 kg·m –3 in Table .…”

Section: Discussionmentioning

confidence: 99%

Densities, Viscosities, and Self-Diffusion Coefficients of Octan-1-ol and Related Ether-Alcohols

Hoffmann,

Gonzalez,

Huynh

et al. 2024

J. Chem. Eng. Data

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Density, viscosity, and self-diffusion coefficients are reported for octan-1-ol and the related ether-alcohols 2-pentoxyethan-1-ol, 3-butoxypropan-1-ol, 4-propoxybutan-1-ol, 5-ethoxypentan-1-ol, and 6-methoxyhexan-1-ol covering temperature ranges from 298.15 to 359.15 K. These new data reveal structure− property relationships affected by the presence and the position of the ether moiety in the molecular structure of the ether-alcohols. Compared to octan-1-ol, the presence of the ether moiety causes an increase in intermolecular hydrogen bonding interactions, resulting in higher densities. The increase in density is less pronounced for those ether-octanols that engage in intramolecular hydrogen bonding. As for the effects of the ether moiety on the dynamics, these are generally faster for the ether-alcohols compared to octan-1ol, suggesting that hydrogen bonding between ether oxygen and hydroxy hydrogen is weaker compared to hydrogen bonding between two hydroxy groups. The activation energies obtained from an Arrhenius analysis are higher for translational motion than for momentum transfer for all alcohols. There are additional finer details across the ether alcohols for these activation barriers. These differences cancel out for the mathematical product of self-diffusion coefficient and viscosity (Dη). The effect of water impurities on the studied properties was also investigated and found to lead to small increases in densities for all alcohols. Viscosities decrease for octan-1-ol and 2-pentoxyethan-1-ol but increase for the other ether-alcohols that can engage in intramolecular hydrogen bonding.

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“…Unfortunately, nucleophilic Scheme 15 Cross-coupling of potassium alkoxymethyltrifluoroborate Scheme 16 Cross-coupling of potassium β-aminoethyltrifluoroborate alkoxyethylmetallics decompose rapidly through facile β-elimination processes [33][34][35][36]. Alkoxyethyltrifluoroborates were thus eventually prepared through the Cu-catalyzed borylation of β-bromoethers with bis(pinacolato)diboron (Scheme 17).…”

Section: Cross-coupling Of Novel Organotrifluoroboratesmentioning

confidence: 99%

Improving Transformations Through Organotrifluoroborates

Traister

Molander

2015

Synthesis and Application of Organoboron Compounds

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Reactions of 2-Halogen Ethers. I. The Action of Magnesium on Alkyl 2-Bromo-ethyl Ethers

Cited by 24 publications

References 0 publications

Suzuki–Miyaura Cross-Coupling of Potassium Alkoxyethyltrifluoroborates: Access to Aryl/Heteroarylethyloxy Motifs

Suzuki–Miyaura Cross-Coupling of Potassium Alkoxyethyltrifluoroborates: Access to Aryl/Heteroarylethyloxy Motifs

Densities, Viscosities, and Self-Diffusion Coefficients of Octan-1-ol and Related Ether-Alcohols

Improving Transformations Through Organotrifluoroborates

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