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inquiryphenylacetylene
methyl trifluoromethanesulfonate
A
(1,4,7,10-tetraoxacyclododecane)
B
[W(CO)5(P(CHCMePh)(CH(SiMe3)2)(OPh))]
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: LiOTf; under Ar, soln. of phenylacetylene (1.0 mmol) added to W complex in THF at -78°C, after 0.5 h of stirring, phenylacetylene added, mixt. heated at reflux for 2 h, cooled to ambient temp., MeOTf added; volatiles evapd. in vac. (ca. 0.01 mbar), raw product purified by columnchromy. (SiO2, -20°C, petroleum ether/Et2O, 10:1), product obtai ned from 2nd fraction, detd. by 1H NMR, 13C NMR, 31P NMR, 29Si NMR, IR, MS; | A n/a B 62% |
ethylene glycol
1,2-bis(2-chloroethoxy)ethane
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
With potassium hydroxide for 0.1h; microwave irradiation; | 37% |
Conditions | Yield |
---|---|
With cyanomethylenetributyl-phosphorane In benzene at 60℃; sealed vessel; | 30% |
With p-toluenesulfonyl chloride; lithium tert-butoxide In tert-butyl alcohol Heating; | 27% |
3-oxa-1,5-dichloropentane
diethylene glycol
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
With lithium hydride In dimethyl sulfoxide Heating; different basis as 'template' agents, other solvents; | 24% |
With lithium hydride In dimethyl sulfoxide Heating; | 24% |
Tetraethylene glycol
A
(1,4,7,10-tetraoxacyclododecane)
B
24-crown-8
C
<36>crown-12
D
48-Crown-16
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃; Further byproducts given; | A 1.4% B 23% C 11% D 4.3% |
Tetraethylene glycol
diethylene glycol
A
(1,4,7,10-tetraoxacyclododecane)
B
18-crown-6 ether
C
24-crown-8
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 60℃; | A n/a B 23% C 3% |
Conditions | Yield |
---|---|
With sodium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 20℃; | A 3% B 12% |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
In methanol at 25℃; Equilibrium constant; enthalpy-entropy compensation for the complexation reactions of crown ethers with alkaline cations; |
Conditions | Yield |
---|---|
In methanol at 25℃; Equilibrium constant; enthalpy-entropy compensation for the complexation reactions of crown ethers with alkaline cations; |
Conditions | Yield |
---|---|
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D; |
A
cyclohexyl-ammonium cation
B
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D; |
Conditions | Yield |
---|---|
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D; |
Conditions | Yield |
---|---|
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D; |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
In acetone Equilibrium constant; various solvents (MeNO2, MeCN, propylene carbonate, MeOH, pyridine), complex formation between crown ethers and lithim ion, effect of solvent of the stability of complexes, 7Li NMR study; |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
In nitromethane Equilibrium constant; various solvents (MeCN, propylene carbonate, Me2CO, MeOH, pyridine), complex formation between crown ethers and lithim ion, effect of solvent of the stability of complexes, formation of 1:1 and 1:2 complexes, 7Li NMR study; |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
With Iodine monochloride In benzene at 24.9℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane-d2 for 480h; |
(1,4,7,10-tetraoxacyclododecane)
sodium trimethylsilanolate
Conditions | Yield |
---|---|
In hexane dry atm.; molar ratio 1:1:2, stirring (room temp., 6 h); filtn., washing (n-hexane), drying (vac.); elem. anal.; | 100% |
(1,4,7,10-tetraoxacyclododecane)
sodium trimethylsilanolate
Conditions | Yield |
---|---|
In hexane dry atm.; molar ratio 1:1:2, stirring (room temp., 6 h); filtn., washing (n-hexane), drying (vac.); elem. anal.; | 100% |
(1,4,7,10-tetraoxacyclododecane)
sodium trimethylsilanolate
Conditions | Yield |
---|---|
In hexane dry atm.; molar ratio 1:1:2, stirring (room temp., 6 h); filtn., washing (n-hexane), drying (vac.); elem. anal.; | 100% |
(1,4,7,10-tetraoxacyclododecane)
sodium trimethylsilanolate
Conditions | Yield |
---|---|
In hexane dry atm.; molar ratio 1:1:2, stirring (room temp., 6 h); filtn., washing (n-hexane), drying (vac.); elem. anal.; | 100% |
tetrahydrofuran
n-butyllithium
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
Stage #1: tetrahydrofuran; n-butyllithium; C12H20B10 Stage #2: (1,4,7,10-tetraoxacyclododecane) In tetrahydrofuran | 100% |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
In tetrahydrofuran for 1h; | 100% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; Inert atmosphere; Schlenk technique; | 100% |
Conditions | Yield |
---|---|
Stage #1: (1,4,7,10-tetraoxacyclododecane); C36H30Be3; phenyllithium In benzene-d6 Stage #2: In benzene-d6 at 80℃; | 100% |
Conditions | Yield |
---|---|
Stage #1: (1,4,7,10-tetraoxacyclododecane); C36H30Be3 In benzene-d6 Stage #2: In benzene-d6 Heating; | 100% |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; | 99% |
(1,4,7,10-tetraoxacyclododecane)
[W(carbonyl)5([bis(trimethylsilyl)methyl]cyanophosphane)]
tert.-butyl lithium
[(OC)5WP(CH(SiMe3)2)CNLi(12-crown-4)]
Conditions | Yield |
---|---|
In diethyl ether; hexane under Ar; soln. of t-BuLi in n-hexane added dropwise at -80°C to stirred soln. of W complex in Et2O and 12-crown-4; warmed slowly to roomtemp. for 3.5 h; solvent removed under vac.; washed with Et2O and n-pentane; dried under reduced pressure; elem. anal.; | 98.3% |
(1,4,7,10-tetraoxacyclododecane)
(Si(o-C6H4PiPr2)3)Fe[(CO)Na(THF)3]
Conditions | Yield |
---|---|
In tetrahydrofuran (Schlenk or glovebox, N2) the soln. of 12-crown-4 in THF was added dropwise to a soln. of complex in THF, stirred for 30 min at room temp.; filtered, volatiles were removed under vac., the solid was washed with pentane; elem. anal.; | 98% |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; Solvent; Inert atmosphere; Schlenk technique; | 98% |
(1,4,7,10-tetraoxacyclododecane)
nitrogen
A
[Mo(N[i-Pr](3,5-C6H3Me2)3N]
Conditions | Yield |
---|---|
In not given at 25°C? 1 atm and in the presence of crown ether (2 equiv. per Na); | A n/a B 97% |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Glovebox; | 97% |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
In tetrahydrofuran standard inert-atmosphere techniques; soln. of (12)crown-4 (0.943 mmol) added to soln. of Sn(OTf)2 (0.479 mmol), stiired for 2 h; solvent removed (in vac.), washed with pentane; elem. anal.; | 96% |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
In diethyl ether under Ar atm. using Schlenk techniques; to soln. of Ba complex in Et2O was added Lewis base; mixt. stirred overnight; solid filtered; washed (pentane); dried under vac.; elem. anal.; | 96% |
Conditions | Yield |
---|---|
In toluene Inert atmosphere; Schlenk technique; | 96% |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 2h; | 96% |
Conditions | Yield |
---|---|
In tetrahydrofuran (N2); using Schlenk techniques; stirring of mixt. of Li(pz) (2 equiv.), Ph3B3O3 (1 equiv.) and 12-crown-4 (2 equiv.) in THF at room temp. for 30min; addn. of hexane; cooling to -5°C overnight; crystn.; rinsing withhexane; drying under reduced pressure; | 95% |
Conditions | Yield |
---|---|
for 0.5h; | 95% |
Conditions | Yield |
---|---|
Stage #1: C44H69ClLiLuO3Si2; pivalaldehyde In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #2: selenium In tetrahydrofuran Inert atmosphere; Stage #3: (1,4,7,10-tetraoxacyclododecane) In tetrahydrofuran for 1h; Inert atmosphere; | 95% |
(1,4,7,10-tetraoxacyclododecane)
uranium(III) tris(1,3-bis-(trimethylsilyl)cyclopentadienyl)
sodium
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.5h; Glovebox; Inert atmosphere; Schlenk technique; | 95% |
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