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Conditions | Yield |
---|---|
With lithium In tetrahydrofuran for 20h; Heating; | 97% |
With tellurium; sodium diethyl phosphite In ethanol for 26h; Ambient temperature; | 70% |
With bis(acetylacetonate)nickel(II); diethylzinc In 1,2-dimethoxyethane; hexane at 80℃; for 48h; Inert atmosphere; | 56% |
With triphenylphosphine; (Cp*ReO)2(μ-O)2 In toluene at 116℃; for 20h; Yield given; |
Conditions | Yield |
---|---|
With hydrogen In hexane at 40℃; under 760.051 Torr; for 5h; | A 3% B 97% |
With hydrogen; Ni-Gr2 In methanol at 30℃; under 22800 Torr; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With hydrogen; ethylenediamine In tetrahydrofuran at 25℃; under 760 Torr; | A 13 % Chromat. B 75 % Chromat. |
2-methyldec-9-enenitrile
1-Decene
Conditions | Yield |
---|---|
With potassium; tert-butyl alcohol In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether at 0℃; for 3h; | 97% |
Conditions | Yield |
---|---|
With hydrogen In toluene at 20℃; under 38002.6 Torr; for 12h; Autoclave; chemoselective reaction; | 95% |
With ammonium chloride; zinc In water for 16h; Reduction; Heating; | 86% |
With palladium on activated charcoal; hydrogen In water at 25℃; under 760.051 Torr; for 1h; | 80% |
Conditions | Yield |
---|---|
With formic acid at 20 - 240℃; Inert atmosphere; | 93% |
With ammonium perrhenate; zinc In benzene at 150℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube; | 58% |
With ammonium metavanadate In propan-1-ol at 225 - 235℃; under 11251.1 Torr; for 16.6667h; Catalytic behavior; Solvent; Autoclave; Inert atmosphere; Sealed tube; | 27% |
1,2-dibromodecane
1-Decene
Conditions | Yield |
---|---|
With sodium hydroxide; sodium tetrahydroborate; 1,2-di(thiophen-2-yl)ditelluride In ethanol; water Ambient temperature; | 92% |
With zinc; titanium tetrachloride In tetrahydrofuran at 0℃; for 3h; | 86% |
With potassium phosphate buffer; glutathione thiol; bis<4-(dimethylamino)phenyl>ditelluride In chloroform; water at 80℃; for 536h; pH 8.9, other reagent: (n-C6H13)2Te/sodium ascorbate/potassium phosphate buffer; | 79% |
Conditions | Yield |
---|---|
Cl(1-)*NPr4(1+) at 50℃; under 22502.3 Torr; for 1h; | A 91.7% B 5.5% |
modified methylalumoxane; C28H24Cl2FeN2S In n-heptane at 30 - 52℃; under 21446.5 Torr; for 0.5h; Product distribution / selectivity; | |
With [η5-(3-SiMe3)C5H3CMe2-3,5-Me2C6H3]Ti(TEA) In toluene at 20℃; under 7500.75 Torr; for 0.25h; Pressure; Reagent/catalyst; Temperature; Inert atmosphere; |
Conditions | Yield |
---|---|
With 18-crown-6 ether; cesium fluoride; bis(tri-n-butyltin)oxide In acetonitrile at 80℃; for 24h; | 90% |
(E)-4-(undec-2-enylsulfinyl)morpholine
1-Decene
Conditions | Yield |
---|---|
With water In 1,4-dioxane at 0℃; for 1h; | 90% |
Conditions | Yield |
---|---|
In pentane for 0.0333333h; Ambient temperature; | 90% |
1-Chloro-1-decyne
1-Decene
Conditions | Yield |
---|---|
Stage #1: 1-Chloro-1-decyne With titanium(IV) isopropylate; isopropylmagnesium bromide In diethyl ether at -50℃; for 2h; Metallation; Stage #2: With hydrogenchloride; water Hydrolysis; | 90% |
(dec-1-ene-1-sulfonyl)benzene
1-Decene
Conditions | Yield |
---|---|
Stage #1: (dec-1-ene-1-sulfonyl)benzene With n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; | 90% |
Stage #1: (dec-1-ene-1-sulfonyl)benzene With n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane at -20 - 20℃; Further stages.; | 90% |
Conditions | Yield |
---|---|
With methoxy(cyclooctadiene)rhodium(I) dimer; bicyclo[2.2.1]hepta-2,5-diene; 3-Methoxybenzoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; | A 90% B n/a |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 250 - 500℃; Large scale; | 89.4% |
(Z)-decenyl phenyl sulfone
1-Decene
Conditions | Yield |
---|---|
Stage #1: (Z)-decenyl phenyl sulfone With n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; | 89% |
1-Decene
Conditions | Yield |
---|---|
Stage #1: (E)-dec-1-enyldicyclohexylborane With 1-hexene; diisobutylaluminium hydride at 0 - 20℃; for 2h; Stage #2: With water at 20℃; for 2h; Further stages.; | 86% |
1-Decene
Conditions | Yield |
---|---|
Stage #1: (E)-1-Methanesulfonyl-dec-1-ene With n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; | 86% |
Stage #1: (E)-1-Methanesulfonyl-dec-1-ene With n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane at -20 - 20℃; Further stages.; | 86% |
2-(but-3-en-1-yl)-2-methyl-1,3-dioxolane
trans-9-octadecene
A
1-Decene
Conditions | Yield |
---|---|
aluminum oxide; tetramethylstannane; rhenium(VII) oxide In chlorobenzene at 25℃; for 3h; Yields of byproduct given; | A n/a B 85.7% |
n-decyl magnesium bromide
benzophenone N-methyl-N,N-pentane-1,5-diylhydrazonium iodide
A
N-methylcyclohexylamine
B
Benzophenone imine
C
decane
D
icosane
E
1-Decene
Conditions | Yield |
---|---|
In diethyl ether Product distribution; Mechanism; Heating; other quaternary hydrazonium salts, other alkylmagnesium halides; | A 85% B 84% C 51% D 21% E 25% |
2-chloro-1-decyl-2-naphthyltellurium dichloride
A
1-Decene
B
di-β-naphthyl ditelluride
Conditions | Yield |
---|---|
With sodium L-ascorbate In methanol; water for 24h; | A n/a B 85% |
(1E)-dec-1-enyl phenyl sulfide
1-Decene
Conditions | Yield |
---|---|
Stage #1: (1E)-dec-1-enyl phenyl sulfide With n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; | 85% |
Stage #1: (1E)-dec-1-enyl phenyl sulfide With n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane at -20 - 20℃; Further stages.; | 85% |
1-Decene
Conditions | Yield |
---|---|
for 0.25h; Irradiation; | 85% |
1-(Brommethylsulfonyl)nonan
1-Decene
Conditions | Yield |
---|---|
With ethanol; sodium for 0.75h; Heating; | 83% |
1-Decene
Conditions | Yield |
---|---|
Stage #1: (E)-1-Propylsulfanyl-dec-1-ene With n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane at -20 - 20℃; Further stages.; | 83% |
Conditions | Yield |
---|---|
With 1-Phenylprop-1-yne; copper In tetrahydrofuran at 25℃; for 3h; | 83% |
bis(η3-allyl)nickel(II) In tetrahydrofuran at -30℃; for 3h; | 91 % Chromat. |
With LaFe0.80Ni0.20O3; buta-1,3-diene at 20℃; for 5h; | 82 %Chromat. |
With cobalt(II) chloride; lithium iodide; isoprene In tetrahydrofuran at -78 - 50℃; for 5h; Inert atmosphere; | 89 %Chromat. |
With cobalt(II) chloride; lithium iodide; isoprene In tetrahydrofuran at -78 - 50℃; for 5h; Inert atmosphere; | 89 %Chromat. |
n-decyl acetate
A
1-hexene
B
1-Decene
C
1,2-dimethylcyclopentane
D
1-Butyl-2-methylcyclopropane
E
1-Methyl-2-pentylcyclopropane
F
cyclopentene
Conditions | Yield |
---|---|
at 495℃; for 0.00727778h; Rate constant; Product distribution; various temp., also in toluene, also with 14C-labelled ester; | A 1.03% B 81.3% C 1.91% D 1.2% E 0.497% F 0.45% |
1-Decene
Conditions | Yield |
---|---|
Stage #1: (E)-1-decenyl isopropyl sulfide With n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; | 81% |
decyl chloride
diethylene glycol
A
1-Decanol
B
1-Decene
C
2-<2-decyloxy)ethoxy>ethanol
Conditions | Yield |
---|---|
With sodium hydroxide; water at 100℃; for 24h; Yields of byproduct given; | A n/a B n/a C 80% |
A
1-Decene
B
(Z)-1-(dimethylfluorosilyl)-1-decene
Conditions | Yield |
---|---|
With 2BF3*3AcOH; chloroacetic acid In hexane at 25℃; for 0.5h; | A 13% B 80% |
(E)-1-tosyl-1-decene
1-Decene
Conditions | Yield |
---|---|
Stage #1: (E)-1-tosyl-1-decene With n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; | 80% |
Stage #1: (E)-1-tosyl-1-decene With n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane at -20 - 20℃; Further stages.; | 80% |
Conditions | Yield |
---|---|
With {(η6-C6H6)Ru(NCCH3)3}{BF4}2; water; hydrogen In benzene at 90℃; under 30400 Torr; for 4h; | 100% |
With hydrogen; Rh on carbon at 75℃; under 3040.2 Torr; for 0.35h; | 100% |
With hydrazine hydrate In ethanol for 24h; Reflux; | 100% |
Conditions | Yield |
---|---|
With hydrogenchloride; oxygen; copper dichloride; palladium dichloride In tetrahydrofuran under 760 Torr; for 4h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With Oxone; osmium (III) chloride In N,N-dimethyl-formamide at 20℃; for 12h; Product distribution; Further Variations:; Catalysts; | 100% |
With sodium periodate; ruthenium trichloride In water; ethyl acetate; acetonitrile for 4h; | 98% |
With Oxone; osmium(VIII) oxide In N,N-dimethyl-formamide; tert-butyl alcohol at 20℃; for 3h; | 93% |
Conditions | Yield |
---|---|
With 1-(2',2'-diphenylvinyl)pyrrolidine In dichloromethane at 20℃; for 16h; Reagent/catalyst; Irradiation; | 100% |
With pyrrolidine; Diphenylacetaldehyde In dichloromethane at 20℃; for 16h; Catalytic behavior; Reagent/catalyst; Wavelength; Inert atmosphere; Irradiation; | 99% |
With rose bengal; sodium thiosulfate In water; acetonitrile at 20℃; for 1h; Reagent/catalyst; Inert atmosphere; Irradiation; | 93% |
Conditions | Yield |
---|---|
Stage #1: 1-Decene; phenylphosphane With 2,2'-azobis(isobutyronitrile) In tetrahydrofuran for 24h; Heating; Stage #2: With dihydrogen peroxide In tetrahydrofuran; water at 0℃; | 100% |
1-Decene
magnesium sulfate
copper(II) chloride
2-methyl decanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; carbon monoxide In tetrahydrofuran; sodium hydroxide; water | 100% |
1-Decene
2-methyldecanoic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; carbon monoxide In methanol | 100% |
1-Decene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
2-decyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With sodium triethylborohydride at 23℃; for 16h; Catalytic behavior; Inert atmosphere; | 100% |
With sodium triethylborohydride In tetrahydrofuran at 23℃; for 16h; Inert atmosphere; Glovebox; | 98% |
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In neat (no solvent) at 20℃; for 24h; Catalytic behavior; regioselective reaction; | 95% |
1-Decene
Conditions | Yield |
---|---|
With oxygen; isobutyraldehyde In acetonitrile at 25℃; for 8h; enantioselective reaction; | 100% |
With titanium(IV) isopropylate; Pentafluorobenzoic acid; C32H22F10N2O2; dihydrogen peroxide In water; 1,2-dichloro-ethane at 20℃; for 10h; Inert atmosphere; enantioselective reaction; | 81% |
With oxygen; isobutyraldehyde In acetonitrile at 20℃; under 1500.15 Torr; for 7h; Autoclave; Green chemistry; | 77 %Chromat. |
Conditions | Yield |
---|---|
With C38H28Au2F12FeN2O8P2S4 In 1,4-dioxane at 45℃; for 20h; Inert atmosphere; Glovebox; Sealed tube; | 100% |
Conditions | Yield |
---|---|
With Cumene hydroperoxide In N,N-dimethyl-formamide at 90℃; for 12h; Flow reactor; | 99.4% |
With [n-Bu4N]4[W10O32]; 1,1,1,3',3',3'-hexafluoro-propanol; dihydrogen peroxide In water at 70℃; for 0.416667h; Catalytic behavior; Reagent/catalyst; Time; Solvent; | 98% |
With NH-pyrazole; water; dihydrogen peroxide; methyltrioxorhenium(VII) In various solvent(s) for 21h; Ambient temperature; | 97% |
1-Decene
1,2-dibromodecane
Conditions | Yield |
---|---|
With ammonium metavanadate; tetrabutylammomium bromide; oxygen; aluminium bromide In acetonitrile at 50℃; for 18h; | 99% |
With aluminum (III) chloride; ammonium metavanadate; tetrabutylammomium bromide; oxygen In 1,2-dimethoxyethane at 50℃; for 18h; | 99% |
With tetrapropylammonium nonabromide In dichloromethane at 0 - 23℃; for 0.0166667h; Inert atmosphere; | 99% |
1-Decene
Se-phenyl(selenothioperoxy)benzoate
S-2-(phenylseleno)-decyl thiobenzoate
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In benzene for 3h; Heating; | 99% |
With 2,2'-azobis(isobutyronitrile) In benzene for 4h; Heating; | 99% |
With 2,2'-azobis(isobutyronitrile) In benzene for 3h; Mechanism; Product distribution; Heating; other reaction time, effect of different additives; | 99% |
1-Decene
(R)-decane-1,2-diol
Conditions | Yield |
---|---|
With AD-mix β In water; tert-butyl alcohol Sharpless Asymmetric Epoxidation; | 99% |
With potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; iodine; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine In water; tert-butyl alcohol at 0℃; for 30h; further cond.: electrolytic method; | 95.8% |
With water; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether In toluene; tert-butyl alcohol at 20℃; for 24h; Sharpless asymmetric dihydroxylation; | 90% |
1-Decene
diphenyl diselenide
acetonitrile
2-acetamido-1-phenylselenodecane
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate electrolytic process; | 99% |
Conditions | Yield |
---|---|
With hydrogen In cyclohexane at 120℃; under 37503.8 Torr; for 4h; Autoclave; | 99% |
With {4,6-bis(tert-butyl)-2-[3,5-bis(tert-butyl)-2-(dinapthyloxyphosphinoxy)-6-methylphenyl]-3-methylphenoxy}dinaphthyloxyphosphine; C30H44O4Ru; hydrogen In toluene at 100℃; under 15001.5 Torr; for 18h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Autoclave; | 66.5% |
With hydrogen; acetylacetonatodicarbonylrhodium(l) under 22502.3 Torr; for 100h; Hydroformylation; |
Conditions | Yield |
---|---|
With silica gel-supported polyphosphoric acid In toluene for 4h; Reflux; | 99% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel(0); C29H41N2; sodium t-butanolate In neat (no solvent) at 50℃; for 21h; Reagent/catalyst; Temperature; Glovebox; Sealed tube; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1-Decene; 3-cyanobromobenzene With tetrakis(triphenylphosphine) palladium(0); 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide In tetrahydrofuran for 4h; Suzuki Coupling; Reflux; Inert atmosphere; Stage #2: Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With pyrrolidine; Diphenylacetaldehyde In dichloromethane at 20℃; for 16h; Inert atmosphere; Irradiation; | 99% |
With 2',4',5',7'-tetrabromofluorescein; sodium thiosulfate In water; acetonitrile at 20℃; for 1h; Inert atmosphere; Irradiation; | 64% |
Conditions | Yield |
---|---|
With C48H60N4O8Pt(2+)*2NO3(1-) In toluene at 80℃; for 1h; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1-Decene With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; regioselective reaction; | 98% |
Stage #1: 1-Decene With triisobutylaluminum; bis-triphenylphosphine-palladium(II) chloride In dichloromethane at 25℃; for 0.5h; Stage #2: With iodine In dichloromethane | 85% |
(i) BH3, THF, (ii) I2, NaOH, MeOH; Multistep reaction; |
Conditions | Yield |
---|---|
With Benzoylformic acid In Petroleum ether for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube; Irradiation; Green chemistry; | 98% |
With potassium carbonate; palladium diacetate; triphenylphosphine In benzene at 100℃; for 3.5h; | 90% |
With C62H44N6Ru(2+)*2Cl(1-) In dimethyl sulfoxide for 24h; Sealed tube; Irradiation; | 90% |
With disodium tetracarbonylferrate In tetrahydrofuran at 25℃; for 16h; Catalytic behavior; Reagent/catalyst; Glovebox; Inert atmosphere; | 83% |
With potassium carbonate; Pd(PPh3)(OAc)2 at 40℃; for 5h; | 88 % Chromat. |
1-Decene
C10H20Cl4Te
Conditions | Yield |
---|---|
With tellurium tetrachloride In chloroform at 0℃; for 3h; | 98% |
1-Decene
A
5-decene
B
4-decene
C
trans-3-decene
D
Decan-2-one
E
2-decene
Conditions | Yield |
---|---|
With oxygen; 2,6-di-O-methyl-β-cyclodextrin; palladium(II) sulfate; H9PV6Mo6O40; copper(II) sulfate In water at 80℃; under 750.06 Torr; for 6h; Mechanism; Product distribution; influence of composition of catalytic mixture on selectivity of reaction; | A n/a B n/a C n/a D 98% E n/a |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel(0); C29H41N2; sodium t-butanolate In neat (no solvent) at 50℃; for 16h; Reagent/catalyst; Temperature; Glovebox; Sealed tube; | 98% |
1-Decene
5-(methoxycarbonyl)benzo[b]furan
methyl 2-decylbenzo[b]furan-5-carboxylate
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel(0); C29H41N2; sodium t-butanolate In toluene at 50℃; for 21h; Glovebox; Sealed tube; | 98% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel(0); C29H41N2; sodium t-butanolate In neat (no solvent) at 65℃; for 22h; Glovebox; Sealed tube; | 98% |
Conditions | Yield |
---|---|
Stage #1: 1-Decene; 4-bromobenzenecarbonitrile With tetrakis(triphenylphosphine) palladium(0); 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide In tetrahydrofuran for 4h; Inert atmosphere; Suzuki Coupling; Reflux; Inert atmosphere; Stage #2: Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With pyrrolidine; Diphenylacetaldehyde In dichloromethane at 20℃; for 16h; Inert atmosphere; Irradiation; | 98% |
With Eosin Y; sodium thiosulfate In acetonitrile at 20℃; for 1h; Inert atmosphere; Irradiation; | 53% |
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