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18-bromo-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]Hexaoxacyclotetradecene
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 1.5h; | 95% |
o-hydroxyphenyl 3,6,9,12-tetraoxa-14-bromotetradecyl ether
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 25℃; | 90.4% |
sodium cation In methanol at 25℃; further catalysts; | |
With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 25℃; Rate constant; other reagent; | 90.4 % Spectr. |
penta(ethylene glycol) bis(p-toluenesulfonate)
benzene-1,2-diol
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating; | 77% |
With sodium hydride In tetrahydrofuran for 7h; Heating; | 40% |
2,2'-(1,2-phenylenedioxy)diethanol
triethylene glycol di-(p-toluenesulfonate)
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating; | 69% |
With potassium tert-butylate 1) THF, RT, 1 h, 2) THF, RT, 24 h; reflux, 48 h; Yield given. Multistep reaction; |
2-[2-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}phenoxy)ethoxy]-1-ethanol
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
With sodium hydroxide; tetra-(n-butyl)ammonium iodide; p-toluenesulfonyl chloride In toluene at 70 - 75℃; for 13h; | 68% |
1,14-dichloro-3,6,9,12-tetraoxatetradecane
benzene-1,2-diol
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
60% |
bis(o-phenylene)glycol ditosylate
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating; | 8% |
benzene-1,2-diol
pentaethylene glycol dimesylate
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In methanol at 25℃; Equilibrium constant; |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In methanol at 25℃; Equilibrium constant; |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In methanol at 25℃; Equilibrium constant; |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In methanol at 25℃; Equilibrium constant; |
Lithium; 2-[2-(2-{2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenolate
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Rate constant; |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In methanol at 25℃; Rate constant; Thermodynamic data; rate constant and activation parameters (ΔHexcit, ΔSexcit) for the cyclization; |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In methanol at 25℃; Rate constant; Thermodynamic data; rate constant and activation parameters (ΔHexcit, ΔSexcit) for the cyclization; |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In methanol at 25℃; Rate constant; Thermodynamic data; rate constant and activation parameters (ΔHexcit, ΔSexcit) for the cyclization; |
2-[2-(2-{2-[2-(2-Bromo-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenolatetetraethyl-ammonium;
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Rate constant; |
Caesium; 2-[2-(2-{2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenolate
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Rate constant; | |
In methanol at 25℃; Rate constant; Thermodynamic data; rate constant and activation parameters (ΔHexcit, ΔSexcit) for the cyclization; |
Sodium; 2-[2-(2-{2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenolate
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Rate constant; | |
In methanol at 25℃; Rate constant; Thermodynamic data; rate constant and activation parameters (ΔHexcit, ΔSexcit) for the cyclization; |
GENERIC INORGANIC CATION; 2-[2-(2-{2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenolate
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Rate constant; | |
In methanol at 25℃; Rate constant; Thermodynamic data; rate constant and activation parameters (ΔHexcit, ΔSexcit) for the cyclization; |
2-[2-(2-{2-[2-(2-Bromo-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenol anion
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Rate constant; | |
In methanol at 25℃; Rate constant; Thermodynamic data; rate constant and activation parameters (ΔHexcit, ΔSexcit) for the cyclization; | |
lithium cation; potassium ion In dimethyl sulfoxide at 25℃; Rate constant; Equilibrium constant; |
Potassium; 2-[2-(2-{2-[2-(2-bromo-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenolate
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Rate constant; | |
In methanol at 25℃; Rate constant; Thermodynamic data; rate constant and activation parameters (ΔHexcit, ΔSexcit) for the cyclization; |
18-bromo-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]Hexaoxacyclotetradecene
A
4'-formyl-benzo-18-crown-6-ether
B
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
With n-butyllithium 1) Et2O, THF, hexane, -60 deg C, 4.0 h; 2) DMF, Et2O, THF, hexane, -60 deg C, 1.2 h; Yield given. Multistep reaction. Yields of byproduct given; |
18-bromo-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]Hexaoxacyclotetradecene
N,N-dimethyl-formamide
A
4'-formyl-benzo-18-crown-6-ether
B
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
With n-butyllithium 1) Et2O, THF, hexane, -60 deg C, 4.0 h; 2) Et2O, THF, hexane, -60 deg C, 1.2 h; Yield given. Multistep reaction. Yields of byproduct given; |
A
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Equilibrium constant; |
A
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Equilibrium constant; |
A
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Equilibrium constant; |
A
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 25℃; Equilibrium constant; |
2-[2-(chloroethoxy)ethoxy]ethanol
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91 percent / K2CO3 / dimethylformamide / 10 h / 95 - 100 °C 2: 68 percent / aq. NaOH; (nC4H9)4NI; p-TsCl / toluene / 13 h / 70 - 75 °C View Scheme |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
(((C6H5)2PCH2CH2P(C6H5)2)Pd(OC6H3ClCHNCH2C6H4NH2))(1+)*BF4(1-)=(((C6H5)2PCH2CH2P(C6H5)2)Pd(OC6H3ClCHNCH2C6H4NH2))BF4
Conditions | Yield |
---|---|
In diethyl ether; dichloromethane under N2 atm. to soln. Pd complex and benzo-18-crown-6 in CH2Cl2 54% soln. HBF4 in Et2O was added and stirred for 5 min; Et2O was added, ppt. was filtered, washed with Et2O and dried in vacuo for 12 h; elem. anal.; | 99% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
acenaphthene quinone
C44H52O13
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In chloroform at 25℃; regioselective reaction; | 98% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
5-nitroisatin
C40H50N2O15
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In chloroform at 25℃; regioselective reaction; | 97% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
4'-nitrobenzo-18-crown-6
Conditions | Yield |
---|---|
With nitric acid In dichloromethane at 20℃; for 24h; | 96% |
With nitric acid In chloroform; acetic acid at 20℃; for 24.5h; | 78% |
With nitric acid; acetic acid In chloroform; water at 20℃; for 24.5h; | 77% |
formaldehyd
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
4',5'-bis(chloromethyl)benzo-18-crown-6
Conditions | Yield |
---|---|
With hydrogenchloride In water for 2.25h; | 96% |
thionicotinamide
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In methanol; ethyl acetate | 96% |
In methanol; ethyl acetate at 20℃; for 72h; | 96% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
diphenyl iodoniumarsenic hexafluoride
Conditions | Yield |
---|---|
Reflux; | 96% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
4',5'-dinitrophenyl crown ether 18C6
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid | 95% |
With sulfuric acid; nitric acid In chloroform at 0 - 20℃; for 48h; | 91% |
Stage #1: 2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin With nitric acid In acetic acid at 15 - 20℃; Stage #2: With nitric acid In acetic acid for 0.5h; cooling; | 88% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
4,5-bis(bromomethyl)benzo<18>crown-6
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid 1) r.t., 1 h; 2) 5 deg C, 2 d; | 95% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
4',5'-bromobenzo-18-crown-6
Conditions | Yield |
---|---|
With dioxane dibromide In tetrahydrofuran for 0.5h; | 90% |
With bromine; iodine; iron In dichloromethane for 16h; Ambient temperature; | 53% |
With bromine; iodine; iron In dichloromethane at 0 - 20℃; for 16h; | 53% |
With bromine; iodine; iron In dichloromethane at 20℃; Inert atmosphere; | 46% |
With bromine; acetic acid Ambient temperature; |
copper(l) iodide
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
potassium iodide
Conditions | Yield |
---|---|
In toluene for 24h; Inert atmosphere; Schlenk technique; | 90% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
potassium bromide
copper(I) bromide
Conditions | Yield |
---|---|
In toluene for 24h; Inert atmosphere; Schlenk technique; | 90% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In toluene for 24h; Inert atmosphere; Schlenk technique; | 90% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
acetic acid
4'-acetylbenzo-18-crown-6
Conditions | Yield |
---|---|
With PPA at 70℃; for 0.666667h; | 88% |
With methanesulfonic acid; phosphorus pentoxide at 20℃; for 6h; | 80% |
With PPA at 80℃; for 3h; |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
hexamethylenetetramine
4'-formyl-benzo-18-crown-6-ether
Conditions | Yield |
---|---|
With trifluoroacetic acid at 85 - 90℃; for 24h; | 86% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
11-aminoundecanoic acid
2,3-<4-(10-Aminodecylcarbonyl)>benzo-18-crown-6
Conditions | Yield |
---|---|
With PPA at 80℃; for 5h; | 85% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
tert-butyl alcohol
4'-tert-Butylbenzo-18-crown-6
Conditions | Yield |
---|---|
With PPA at 60℃; for 5h; | 85% |
With PPA at 70℃; for 5h; | 85% |
With sulfuric acid; sodium perchlorate In chloroform Heating; or KClO4; | 15% |
2,4-dithiouracil
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
Conditions | Yield |
---|---|
In methanol; ethyl acetate at 20℃; | 85% |
tert-Amyl alcohol
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
4'-tert-Amylbenzo-18-crown-6
Conditions | Yield |
---|---|
With PPA at 70℃; for 5h; | 82% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
2-iodo-6,7,9,10,12,13,15,16,18,19-decahydro-5,8,11,14,17,20-hexaoxabenzocyclooctadecene
Conditions | Yield |
---|---|
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid | 81% |
With N-iodo-succinimide In water at 20℃; for 2h; | 66% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
3-nitro-1,2,4-triazole
Conditions | Yield |
---|---|
In hexane; acetone at 20℃; | 81% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
propionic acid
1-(2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin-18-yl)-1-propanone
Conditions | Yield |
---|---|
With PPA | 80% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
butyric acid
1-(6,7,9,10,12,13,15,16,18,19-Decahydro-5,8,11,14,17,20-hexaoxa-benzocyclooctadecen-2-yl)-butan-1-one
Conditions | Yield |
---|---|
With PPA | 80% |
fluorobenzene
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
tricarbonyl(cycloheptatriene)molybdenum(0)
Conditions | Yield |
---|---|
Stage #1: potassium graphite; C15Fe5O14 In tetrahydrofuran at -20 - 20℃; for 8h; Inert atmosphere; Stage #2: fluorobenzene; 2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin; tricarbonyl(cycloheptatriene)molybdenum(0) In tetrahydrofuran Inert atmosphere; | 79% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
18-bromo-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]Hexaoxacyclotetradecene
Conditions | Yield |
---|---|
With C4H8O2*Br2 In tetrahydrofuran for 0.333333h; Ambient temperature; | 78% |
With dioxane dibromide In tetrahydrofuran for 0.166667h; | 78% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
acetic anhydride
4'-acetylbenzo-18-crown-6
Conditions | Yield |
---|---|
With PPA In acetic acid at 60℃; | 78% |
With phosphoric acid; acetic acid at 60℃; for 24h; | 70% |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
1,3,4,6-bis(2-oxapropylene)tetrahydro-3a,6a-diphenylimidazo<4,5-d>imidazole-2,5(1H,3H)-dione
C52H62N4O14
Conditions | Yield |
---|---|
With polyphosphoric acid at 80 - 85℃; for 0.5h; | 78% |
With polyphosphoric acid at 80℃; |
2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin
4,6,8-trimethylazulene
(6,7,9,10,12,13,15,16,18,19-decahydro-5,8,11,14,17-hexaoxa-benzocyclooctadecen-2-yl)-4,6,8-trimethylazulen-1-yl-diazene
Conditions | Yield |
---|---|
Stage #1: 2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin With hydrogenchloride In water at 0℃; Stage #2: With sodium nitrite In water at 5℃; for 0.166667h; Stage #3: 4,6,8-trimethylazulene With potassium carbonate In methanol; water at 0℃; for 1h; | 78% |
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