Complexation of aryldiazonium ions by glymes

Bartsch, Richard A.; Juri, Pedro N.

doi:10.1016/s0040-4039(01)93518-x

Cited by 12 publications

(4 citation statements)

References 14 publications

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“…Timko et al 138 compared the complexation of t -butylammonium thiocyanate with pentaglyme and 18-crown-6 in chloroform at 24 °C, and found a macrocyclic effect of 18,700. The Bartsch group 139 studied the complexing effect of p-tert -butylbenzendiazonium tetrafluoroborate with glymes in 1,2-dichloroethane at 50 °C, and suggested a macrocyclic effect of ~30 when comparing the complexation constants ( K ) for pentaglyme and 18-crown-6 with aryldiazolium ions. They also observed that the K value is basically constant (~2) for diglyme, triglyme and tetraglyme, followed by a steady increase for pentaglyme (4.78), hexaglyme (7.71), and heptaglyme (11.8) due to an increasing ability of the glyme to assume a pseudo cyclic structure; however, there is a drastic drop in K value for octaglyme (3.81) followed by a gradual increase for nonaglyme (6.32) and decaglyme (13.6).…”

Section: Physicochemical and Metal Complexing Properties Of Glymesmentioning

confidence: 99%

Glymes as versatile solvents for chemical reactions and processes: from the laboratory to industry

2014

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Glymes, also known as glycol diethers, are saturated non-cyclic polyethers containing no other functional groups. Most glymes are usually less volatile and less toxic than common laboratory organic solvents; in this context, they are more environmentally benign solvents. However, it is also important to point out that some glymes could cause long-term reproductive and developmental damages despite their low acute toxicities. Glymes have both hydrophilic and hydrophobic characters that common organic solvents are lack of. In addition, they are usually thermally and chemically stable, and can even form complexes with ions. Therefore, glymes are found in a broad range of laboratory applications including organic synthesis, electrochemistry, biocatalysis, materials, and Chemical Vapor Deposition (CVD), etc. In addition, glyme are used in numerous industrial applications, such as cleaning products, inks, adhesives and coatings, batteries and electronics, absorption refrigeration and heat pumps, as well as pharmaceutical formulations, etc. However, there is a lack of comprehensive and critical review on this attractive subject. This review aims to accomplish this task by providing an in-depth understanding of glymes’ physicochemical properties, toxicity and major applications.

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Section: Physicochemical and Metal Complexing Properties Of Glymesmentioning

confidence: 99%

Glymes as versatile solvents for chemical reactions and processes: from the laboratory to industry

2014

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“…A linear regression analysis of the viscosity and density values was attempted to estimate the coefficients, a and b, of eq 7. ln(p or rf) = a + b{T/K) (7) The correlation coefficient values, r, and the estimated values of a and b are given in Table 2.…”

Section: >/Kmentioning

confidence: 99%

“…Because the reaction conditions involved a two-phase system, initially a phasetransfer catalyst (tetrabutylammonium hydrogen sulfate) was used in order to promote the reaction (5,6). However, since polyglycols are known to function as phase-transfer catalysts (7), reactions were also run in the absence of tetrabutylammonium hydrogen sulfate. The latter conditions resulted in a considerably simpler workup, and in addition, infrared analysis indicated no difference in the extent of reaction.…”

Section: Introductionmentioning

confidence: 99%

Densities, Viscosities, Speeds of Sound, and Water Solubilities of Some Polypropylene Glycol Ether Derivatives in the Temperature Range 273.15-323.15 K

Idoux¹,

McCurry²,

Aminabhavi³

1994

J. Chem. Eng. Data

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“…Instead, we chose to work in F 2CIC-CFCI2 • Under these conditions, reasonable yields of cyclization products were obtained for a number of substrates [26]. Two successful cyclizations are illustrated in his co-workers have adapted many of the crown catalyzed transformations to oligoethylene glycol catalysis [37]. In addition to gegenion metathesis [IS} certain soaps [38] have been used as catalysts for these reactions.…”

Section: The Phase Transfer Pschorr Cyclization Thementioning

confidence: 99%

Applications of Phase Transfer Catalysis to Arenediazonium Cation Chemistry

Gokel

Ahern

Beadle

et al. 1985

Israel Journal of Chemistry

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Arenediazonium cations have been known for many years but the synthetic utility has been diminished by their lack of stability and by their proclivity for undergoing sundry side reactions. Arenediazonium BF4 and PF. salts are generally stable solids, but are relatively insoluble in nonpolar organic media. Crown complexationand other forms of phase transfer catalysis increase solubility and allow numerous synthetic transformations to be conducted in good yield. The yield improvements result from a reduction in competing side reactions rather than any fundamental change in mechanism. The reactions to which the phase transfer technique is successfully applied are diazo coupling, reduction, halogenation, arylation and cyclization. In the latter case, the use of potassium superoxide is sometimes a more efficacious reagent than potassium acetate. The phase transfer approach can be used in the high yield synthesis of arenediazosulfones and arenediazocyanides. The latter undergo cycloaddition with many dienes to yield pyridazine derivatives.

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Complexation of aryldiazonium ions by glymes

Cited by 12 publications

References 14 publications

Glymes as versatile solvents for chemical reactions and processes: from the laboratory to industry

Glymes as versatile solvents for chemical reactions and processes: from the laboratory to industry

Densities, Viscosities, Speeds of Sound, and Water Solubilities of Some Polypropylene Glycol Ether Derivatives in the Temperature Range 273.15-323.15 K

Applications of Phase Transfer Catalysis to Arenediazonium Cation Chemistry

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