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Conditions | Yield |
---|---|
With silver(II) fluoride at 225 - 330℃; | |
With nickel(II) fluoride; cobalt (III) fluoride; fluorine 1.) 450 deg C, 2.) 450-500 deg C; Multistep reaction; | |
With silver(II) fluoride at 225 - 330℃; |
Conditions | Yield |
---|---|
With silver plated copper; fluorine at 350 - 380℃; |
Conditions | Yield |
---|---|
With silver(II) fluoride at 225 - 330℃; | |
With silver(II) fluoride at 225 - 330℃; |
Conditions | Yield |
---|---|
With silver(II) fluoride at 225 - 330℃; | |
With silver(II) fluoride at 225 - 330℃; |
Conditions | Yield |
---|---|
With antimony pentafluoride at 300℃; |
octadecafluorodecahydronaphthalene (cis+trans)
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: C10F14, C10F13; react. of Mn complex with large excess of perfluorodecalin (molar ratio1:19) in THF at 20°C; detd. by GC and GC/MS; | 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran-d8 at 20℃; for 72h; | A n/a B 94% |
octadecafluorodecahydronaphthalene (cis+trans)
2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-8-imino-3,4,5,6,7,8-hexahydro-2H-naphthalene-1,4a-diamine
Conditions | Yield |
---|---|
With ammonia; mercury Irradiation; | 92% |
octadecafluorodecahydronaphthalene (cis+trans)
Conditions | Yield |
---|---|
In tetrahydrofuran for 1h; Inert atmosphere; | 68% |
octadecafluorodecahydronaphthalene (cis+trans)
sodium thiophenolate
octakis(phenylthio)naphthalene
Conditions | Yield |
---|---|
With 1,3-dimethyl-2-imidazolidinone at 50 - 60℃; for 240h; | 65% |
Conditions | Yield |
---|---|
With benzophenone; sodium In tetrahydrofuran for 1.5h; -70 deg C to rt; | 62% |
With benzophenone; sodium In tetrahydrofuran for 1.5h; other substrates, other reducing agents, other temperature; | 62% |
With cobaltocene; lithium trifluoromethanesulfonate In diethyl ether for 12h; Ambient temperature; | 53% |
octadecafluorodecahydronaphthalene (cis+trans)
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane under Ar or N2; addn. of perfluorodecalin to soln. of YbCp2(DME) in DME, stirring for 48 h at room temp.; filtration of ppt., washing with DME, drying for 3 h under vac.; elem. anal.; | 49% |
octadecafluorodecahydronaphthalene (cis+trans)
A
octafluoronaphthalene
B
perfluorotetralin
Conditions | Yield |
---|---|
With sodium oxalate at 465℃; Product distribution; Further Variations:; various carrier gases, preheat time and addition time of substrate; Aromatisation; | A 42% B 10% |
With sodium oxalate at 425℃; |
octadecafluorodecahydronaphthalene (cis+trans)
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere; | 40% |
octadecafluorodecahydronaphthalene (cis+trans)
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere; | 38% |
octadecafluorodecahydronaphthalene (cis+trans)
hexadecafluoro-bicyclo<4.4.0>dec-1(6)-ene
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethyl-para-phenylenediamine In hexane; N,N-dimethyl-formamide for 4h; Irradiation; | 35% |
With pyrographite at 450℃; for 2h; Product distribution; further reagent, temperature, substituted perfluorodecalins; | |
With tetra-(n-butyl)ammonium iodide In tetrahydrofuran Elimination; Irradiation; |
octadecafluorodecahydronaphthalene (cis+trans)
sodium cyclohexanethiolate
octakis(cyclohexylsulfanyl)naphthalene
Conditions | Yield |
---|---|
With 1,3-dimethyl-2-imidazolinone at 60℃; for 336h; | 34% |
Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran)
octadecafluorodecahydronaphthalene (cis+trans)
tetra((μ-fluoro)bis(methylcyclopentadienyl)ytterbium(III))
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane under Ar or N2; addn. of DME to Yb(MeCp)2(THF) and perfluorodecalin, stirring for 24 h at room temp.; filtration of solid, washing with DME, drying for 3 h under vac.; elem.anal.; | 25% |
Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran)
octadecafluorodecahydronaphthalene (cis+trans)
di((μ-fluoro)bis(methylcyclopentadienyl)(tetrahydrofuran)ytterbium(III))
Conditions | Yield |
---|---|
In tetrahydrofuran under Ar or N2; stirring Yb(MeCp)2(THF) and perfluorodecalin for 48 h in THF at room temp., warming up to 50°C for 2 h, slow cooling; filtration of ppt., washing with THF; elem. anal.; | 24% |
Conditions | Yield |
---|---|
With silver(II) fluoride at 225 - 330℃; | |
With nickel(II) fluoride; cobalt (III) fluoride; fluorine 1.) 450 deg C, 2.) 450-500 deg C; Multistep reaction; | |
With silver(II) fluoride at 225 - 330℃; |
Conditions | Yield |
---|---|
With silver plated copper; fluorine at 350 - 380℃; |
Conditions | Yield |
---|---|
With silver(II) fluoride at 225 - 330℃; | |
With silver(II) fluoride at 225 - 330℃; |
Conditions | Yield |
---|---|
With silver(II) fluoride at 225 - 330℃; | |
With silver(II) fluoride at 225 - 330℃; |
Conditions | Yield |
---|---|
With antimony pentafluoride at 300℃; |
octadecafluorodecahydronaphthalene (cis+trans)
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: C10F14, C10F13; react. of Mn complex with large excess of perfluorodecalin (molar ratio1:19) in THF at 20°C; detd. by GC and GC/MS; | 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran-d8 at 20℃; for 72h; | A n/a B 94% |
octadecafluorodecahydronaphthalene (cis+trans)
2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-8-imino-3,4,5,6,7,8-hexahydro-2H-naphthalene-1,4a-diamine
Conditions | Yield |
---|---|
With ammonia; mercury Irradiation; | 92% |
octadecafluorodecahydronaphthalene (cis+trans)
Conditions | Yield |
---|---|
In tetrahydrofuran for 1h; Inert atmosphere; | 68% |
octadecafluorodecahydronaphthalene (cis+trans)
sodium thiophenolate
octakis(phenylthio)naphthalene
Conditions | Yield |
---|---|
With 1,3-dimethyl-2-imidazolidinone at 50 - 60℃; for 240h; | 65% |
Conditions | Yield |
---|---|
With benzophenone; sodium In tetrahydrofuran for 1.5h; -70 deg C to rt; | 62% |
With benzophenone; sodium In tetrahydrofuran for 1.5h; other substrates, other reducing agents, other temperature; | 62% |
With cobaltocene; lithium trifluoromethanesulfonate In diethyl ether for 12h; Ambient temperature; | 53% |
octadecafluorodecahydronaphthalene (cis+trans)
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane under Ar or N2; addn. of perfluorodecalin to soln. of YbCp2(DME) in DME, stirring for 48 h at room temp.; filtration of ppt., washing with DME, drying for 3 h under vac.; elem. anal.; | 49% |
octadecafluorodecahydronaphthalene (cis+trans)
A
octafluoronaphthalene
B
perfluorotetralin
Conditions | Yield |
---|---|
With sodium oxalate at 465℃; Product distribution; Further Variations:; various carrier gases, preheat time and addition time of substrate; Aromatisation; | A 42% B 10% |
With sodium oxalate at 425℃; |
octadecafluorodecahydronaphthalene (cis+trans)
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere; | 40% |
octadecafluorodecahydronaphthalene (cis+trans)
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere; | 38% |
octadecafluorodecahydronaphthalene (cis+trans)
hexadecafluoro-bicyclo<4.4.0>dec-1(6)-ene
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethyl-para-phenylenediamine In hexane; N,N-dimethyl-formamide for 4h; Irradiation; | 35% |
With pyrographite at 450℃; for 2h; Product distribution; further reagent, temperature, substituted perfluorodecalins; | |
With tetra-(n-butyl)ammonium iodide In tetrahydrofuran Elimination; Irradiation; |
octadecafluorodecahydronaphthalene (cis+trans)
sodium cyclohexanethiolate
octakis(cyclohexylsulfanyl)naphthalene
Conditions | Yield |
---|---|
With 1,3-dimethyl-2-imidazolinone at 60℃; for 336h; | 34% |
Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran)
octadecafluorodecahydronaphthalene (cis+trans)
tetra((μ-fluoro)bis(methylcyclopentadienyl)ytterbium(III))
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane under Ar or N2; addn. of DME to Yb(MeCp)2(THF) and perfluorodecalin, stirring for 24 h at room temp.; filtration of solid, washing with DME, drying for 3 h under vac.; elem.anal.; | 25% |
Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran)
octadecafluorodecahydronaphthalene (cis+trans)
di((μ-fluoro)bis(methylcyclopentadienyl)(tetrahydrofuran)ytterbium(III))
Conditions | Yield |
---|---|
In tetrahydrofuran under Ar or N2; stirring Yb(MeCp)2(THF) and perfluorodecalin for 48 h in THF at room temp., warming up to 50°C for 2 h, slow cooling; filtration of ppt., washing with THF; elem. anal.; | 24% |
octadecafluorodecahydronaphthalene (cis+trans)
sodium cyclopentanethiolate
oktakis(cyclopentylthio)naphthalene
Conditions | Yield |
---|---|
With 1,3-dimethyl-2-imidazolinone at 60℃; for 336h; | 23% |
Conditions | Yield |
---|---|
iron at 460 - 500℃; |
Conditions | Yield |
---|---|
Equilibrium constant; |
octadecafluorodecahydronaphthalene (cis+trans)
alpha cyclodextrin
Conditions | Yield |
---|---|
Equilibrium constant; |
octadecafluorodecahydronaphthalene (cis+trans)
A
octafluoronaphthalene
B
1,3,4,5,6,7,8-heptafluoronaphthalene
Conditions | Yield |
---|---|
With zirconocene dichloride; magnesium; mercury dichloride In tetrahydrofuran for 2h; Ambient temperature; | A 55 % Spectr. B 35 % Spectr. |
octadecafluorodecahydronaphthalene (cis+trans)
2,6-dihydrogenhexafluoronaphthalene
Conditions | Yield |
---|---|
With zirconocene dichloride; magnesium; mercury dichloride In tetrahydrofuran for 14h; Ambient temperature; |
octadecafluorodecahydronaphthalene (cis+trans)
perfluorobicyclo<4.4.0>dec-1(2)-en-6-ol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Bu4NI*xH2O / tetrahydrofuran / Irradiation 2: Bu4NI*xH2O / tetrahydrofuran / Irradiation View Scheme |
octadecafluorodecahydronaphthalene (cis+trans)
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Bu4NI*xH2O / tetrahydrofuran / Irradiation 2: Bu4NI*xH2O / tetrahydrofuran / Irradiation 3: Bu4NI*xH2O / tetrahydrofuran / Irradiation View Scheme |
Yb(2,6-di-tert-butylphenolate)2(THF)3
octadecafluorodecahydronaphthalene (cis+trans)
di(bis(2,6-di-tert-butylphenolato)(μ-fluoro)(tetrahydrofuran)ytterbium(III))
Conditions | Yield |
---|---|
In tetrahydrofuran under Ar or N2; stirring Yb complex and perfluorodecalin in THF at roomtemp. for 48 h, heating to 50°C, cooling to room temp.; filtration of solid, washing with THF, drying for at least 3 h under vac.; elem. anal.; |
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