Conditions | Yield |
---|---|
In liquid sulphur dioxide Ambient temperature; | 99% |
With bromine chloride | 67 % Spectr. |
With (allylsulfonyl)benzene In Cyclohexane-d12; toluene at 130℃; for 36.5h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; | 95 % Spectr. |
With diphenyl disulfone In chloroform-d1 at 80℃; for 1h; Kinetics; |
Conditions | Yield |
---|---|
Stage #1: methyllithium; cyclopentanone at -10 - 0℃; for 0.5h; Stage #2: With toluene-4-sulfonic acid In 1,2-dichloro-ethane Reflux; | 96% |
With acid |
Conditions | Yield |
---|---|
95% | |
With iodine; oxalic acid | 87% |
With iodine Erhitzen des erhaltenen Gemisches von 1-Methyl-cyclopenten und Methylencyclopentan mit Essigsaeure und wenig Toluol-4-sulfonsaeure; |
Conditions | Yield |
---|---|
Stage #1: methyl magnesium iodide; cyclopentanone In diethyl ether for 1h; Heating; Stage #2: With iodine In toluene for 3h; Heating; | 94% |
In diethyl ether for 3h; Ambient temperature; | 34.8% |
2) dehydration; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
In diethyl ether for 1h; | 87% |
(hex-5-enyl)magnesium bromide
A
1-methylcyclopent-1-ene
Conditions | Yield |
---|---|
With isopropylmagnesium bromide; bis(cyclopentadienyl)titanium dichloride In diethyl ether at 36℃; for 5h; | A 66% B n/a |
Dimethyl ether
cyclopentene
B
propene
C
ethene
D
1-methylcyclopent-1-ene
E
benzene
Conditions | Yield |
---|---|
MFI280 zeolite at 400℃; under 750.075 Torr; for 20h; Product distribution / selectivity; Gas phase; | A 59.5% B 22.9% C 6% D 9.5% E 2.1% |
MTT47 zeolite at 400℃; under 750.075 Torr; for 20h; Product distribution / selectivity; Gas phase; | A 52.2% B 6.7% C 1.4% D 39.3% E 0.4% |
cyclohexene
A
hexane
B
methyl-cyclopentane
C
1-methylcyclopent-1-ene
Conditions | Yield |
---|---|
ultrastabilized Y zeolite at 350℃; for 0.0333333h; | A 5.6% B 57.7% C 8.3% |
1,5-Hexadien
A
(E,Z)-2,4-hexadiene
B
(E)-1,4-hexadiene
C
methylenecyclopentane
D
1-methylcyclopent-1-ene
Conditions | Yield |
---|---|
With isopropylmagnesium bromide; bis(cyclopentadienyl)titanium dichloride In diethyl ether at 20℃; for 3h; Further byproducts given. Yields of byproduct given; | A n/a B n/a C n/a D 57% E n/a |
cyclohexene
A
methylenecyclopentane
B
1-methylcyclopent-1-ene
C
3-methyl-1-cyclopentene
Conditions | Yield |
---|---|
ultrastabilized Y zeolite at 450℃; for 1h; | A 1.7% B 54.4% C 9.9% |
cyclohexene
A
1-methylcyclopent-1-ene
B
4-methylcyclopentene
C
3-methyl-1-cyclopentene
Conditions | Yield |
---|---|
ultrastabilized Y zeolite at 450℃; for 1h; | A 54.4% B 4.9% C 9.9% |
aluminum hydroxide contg. TiO2 and Na2O at 350℃; Kinetics; | |
With hydrogenchloride; water In decalin at 225℃; for 49h; Product distribution; Mechanism; in sealed tube; also with DCl/D2O, deuteration investigated; also at 175 deg C; | A 45.2 % Chromat. B n/a C n/a |
cyclohexene
A
hexane
B
methylenecyclopentane
C
methyl-cyclopentane
D
1-methylcyclopent-1-ene
E
4-methylcyclopentene
F
3-methyl-1-cyclopentene
Conditions | Yield |
---|---|
ultrastabilized pprotonic Y zeolite In gas at 350℃; for 1h; Product distribution; Kinetics; other temperatures, other products; | A 0.5% B 1.4% C 1% D 19.6% E 1.8% F 3.6% |
Conditions | Yield |
---|---|
With formaldehyd; ruthenium (III) bromide; hydrogen bromide; hydrogen; tetrabutyl phosphonium bromide In water at 200℃; under 30003 Torr; for 8h; | 13% |
Conditions | Yield |
---|---|
With formaldehyd; ruthenium (III) bromide; hydrogen bromide; hydrogen; tetrabutyl phosphonium bromide In water at 200℃; under 30003 Torr; for 8h; | A 12% B 7% |
Conditions | Yield |
---|---|
at 190 - 200℃; |
methyl magnesium iodide
1-chloro-1-methylcyclopentane
A
1,1-Dimethylcyclopentane
B
1-methylcyclopent-1-ene
1-bromo-1-methyl-cyclopentane
1-methylcyclopent-1-ene
Conditions | Yield |
---|---|
With quinoline at 190 - 200℃; | |
With 1,3,5-triphenylverdasyl at 25℃; Rate constant; other solvents; | |
In ethanol at 25℃; Kinetics; Further Variations:; Solvents; |
Conditions | Yield |
---|---|
With water at 35℃; | |
With quinoline at 160 - 190℃; | |
With sodium hydroxide In water at 20℃; for 2h; Dehydrochlorination; elimination; | |
With 1,3,5-triphenylverdazyl In acetonitrile at 25℃; Kinetics; Further Variations:; Solvents; Temperatures; | |
With 1,3,5-triphenylverdazyl In methanol at 25℃; Kinetics; Further Variations:; Solvents; |
1-chloro-1-methylcyclopentane
A
1-methylcyclopent-1-ene
B
1-methylcyclopentanol
Conditions | Yield |
---|---|
With water In ethanol at 30℃; Rate constant; solvolysis reaction; | |
With calcium hydroxide; water at 35℃; |
1-methylcyclopentyl acetate
A
methylenecyclopentane
B
1-methylcyclopent-1-ene
Conditions | Yield |
---|---|
at 450℃; |
1-methylcyclopentyl acetate
1-methylcyclopent-1-ene
Conditions | Yield |
---|---|
at 450℃; |
3-methylcyclopentanol
1-methylcyclopent-1-ene
Conditions | Yield |
---|---|
With sulfuric acid |
1-chloro-2-methyl-cyclopentane
1-methylcyclopent-1-ene
Conditions | Yield |
---|---|
With quinoline at 160 - 190℃; |
cyclopentylmethyl acetate
A
methylenecyclopentane
B
1-methylcyclopent-1-ene
Conditions | Yield |
---|---|
at 450 - 570℃; |
1-methyl-cyclopentanecarboxylic acid phenyl ester
A
1-methylcyclopent-1-ene
B
phenol
Conditions | Yield |
---|---|
at 390℃; im Rohr; |
Conditions | Yield |
---|---|
at 90 - 120℃; |
Conditions | Yield |
---|---|
Erhitzen des Reaktionsprodukts mit Chinolin auf 190-200grad; |
methyl cyclohexane
1-methylcyclopent-1-ene
Conditions | Yield |
---|---|
With chromium (III)-oxide-aluminium oxide contacts at 550℃; |
Conditions | Yield |
---|---|
at 200 - 300℃; Leiten ueber zuvor mit Phosphorsaeure behandeltes Kieselgur; | |
at 400 - 500℃; Leiten ueber γ-Aluminiumoxyd; |
1-methylcyclopent-1-ene
propionaldehyde
(methyl-2' cyclopentyl)-1 propanone-1
Conditions | Yield |
---|---|
With dibenzoyl peroxide at 90℃; for 10h; | 100% |
1-methylcyclopent-1-ene
1,2-epoxy-1-methylcyclopentane
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 5 - 20℃; Inert atmosphere; | 99% |
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 24℃; for 4h; | 84% |
With gallium oxide; dihydrogen peroxide; acetonitrile at 89.84℃; for 4h; Sealed tube; | 53% |
1-methylcyclopent-1-ene
(R)-methyl 2-(cyclopentenylmethyl)-3,3,3-trifluoro-2-hydroxypropanoate
Conditions | Yield |
---|---|
With 2,6-bis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine; indium(III) chloride; silver hexafluoroantimonate In 1,2-dichloro-ethane at 20℃; Ionic liquid; Molecular sieve; optical yield given as %ee; enantioselective reaction; | 98% |
glyoxylic acid ethyl ester
1-methylcyclopent-1-ene
ethyl (R)-3-(cyclopent-1-en-1-yl)-2-hydroxypropanoate
Conditions | Yield |
---|---|
With 2,6-bis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine; silver hexafluoroantimonate; indium(III) chloride In 1,2-dichloro-ethane at 20℃; for 16h; Molecular sieve; Inert atmosphere; stereoselective reaction; | 98% |
1,1-Diphenylmethanol
1-methylcyclopent-1-ene
((2-methylcyclopent-1-enyl)methylene)dibenzene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In ethylene dibromide at 60℃; Air atmosphere; regioselective reaction; | 96% |
With N-octadecyl-N-(4-sulfobutyl)pyrrolidinium trifluoromethanesulfonate In dichloromethane at 80℃; for 6h; | 92% |
1-methylcyclopent-1-ene
2-Iodo-2-cyanopent-4-ynenitrile
trans-Propargyl-(2-iodo-2-methylcyclopentyl)-malononitrile
Conditions | Yield |
---|---|
In benzene at 80℃; for 24h; | 95% |
Conditions | Yield |
---|---|
With air In tetrahydrofuran byproducts: methylcyclopentane; N2-atmosphere; treatment of B2H6 with olefin, addn. of MeSH (stirring), injecting small amt. of air (in two steps during 2 h), stirring for 12 h; evapn. of volatiles (reduced pressure), fractional distn. (reduced pressure); | 95% |
Conditions | Yield |
---|---|
With 9-(2-mesityl)-10-methylacridinium perchlorate In 1,2-dichloro-ethane at 20℃; Irradiation; Green chemistry; regioselective reaction; | 94% |
carbon monoxide
1-methylcyclopent-1-ene
trans-2-Methylcyclopentanecarbaldehyde
Conditions | Yield |
---|---|
With dicarbonylacetylacetonato rhodium (I); C37H50NO4P; hydrogen In toluene at 100℃; under 15001.5 Torr; for 12h; Autoclave; regioselective reaction; | 92% |
1-methylcyclopent-1-ene
1,3-Dimethoxybenzene
2,4-dimethoxy-1-(1-methylcyclopentyl)benzene
Conditions | Yield |
---|---|
With calcium(II) bis(trifluoromethanesulfonyl)imide; tert-butylammonium hexafluorophosphate(V) In dichloromethane at 20℃; for 1h; | 91% |
trichloro-acetyl bromide
1-methylcyclopent-1-ene
7,7-dichloro-1-methylbicyclo[3.2.0]heptan-6-one
Conditions | Yield |
---|---|
With zinc In diethyl ether Heating; | 90% |
1-methylcyclopent-1-ene
5-cyano-1H-pyrazole-4-carboxylic acid, ethyl ester
5-cyano-1-(1-methylcyclopentyl)-1H-pyrazole-4-carboxylic acid, ethyl ester
Conditions | Yield |
---|---|
With sulfuric acid In dichloromethane; acetonitrile for 2h; Ambient temperature; | 90% |
1-methylcyclopent-1-ene
trichloroacetonitrile
2,2,2-Trichloro-1-(2-methyl-cyclopent-2-enyl)-ethanone
Conditions | Yield |
---|---|
With boron trifluoride; water In dichloromethane at -78℃; | 90% |
1-methylcyclopent-1-ene
[Chloro-(3,4-dichloro-phenylsulfanyl)-methyl]-trimethyl-silane
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane at -20℃; for 0.5h; | 90% |
1-methylcyclopent-1-ene
(1S,2S)-trans-2-methylcyclopentanol
Conditions | Yield |
---|---|
With (R,R)-C6H12BH2(1-)*Li(1+)*OEt2; methyl iodide In diethyl ether for 9.5h; Ambient temperature; | 89% |
Conditions | Yield |
---|---|
With dichlorobis(tri-O-tolylphosphine)palladium; potassium carbonate In N,N-dimethyl acetamide; ethylene glycol at 75℃; for 22h; Schlenk technique; Inert atmosphere; Sealed tube; | 88% |
Conditions | Yield |
---|---|
Stage #1: 1-methylcyclopent-1-ene With ozone In dichloromethane at -78℃; Stage #2: With triphenylphosphine In dichloromethane at -78 - 20℃; for 10h; | 87% |
Stage #1: 1-methylcyclopent-1-ene With ozone In dichloromethane at -78 - 20℃; Stage #2: With dimethylsulfide In dichloromethane at 20℃; for 5h; Stage #3: With triphenylphosphine In dichloromethane at 20℃; for 5h; Further stages.; | 87% |
Stage #1: 1-methylcyclopent-1-ene With osmium(VIII) oxide; 4-methylmorpholine N-oxide; tert-butyl alcohol In acetone at 20℃; for 4h; Stage #2: With sodium periodate In water at 20℃; for 1h; | 85% |
Conditions | Yield |
---|---|
With zeolite-P at 80℃; for 3h; | 86.4% |
cationite KU-23 at 80℃; for 5h; Product distribution; other alkyl- and alkenylcyclenes; var. temp. and time; | |
cationite KU-23 at 80℃; for 5h; |
Conditions | Yield |
---|---|
With diethylzinc In cyclohexane for 120h; Ambient temperature; | 86% |
With iodine; copper; zinc In diethyl ether |
Conditions | Yield |
---|---|
With Lindlar's catalyst; ozone-containing oxygen; ammonium chloride; sodium methylate 1) -75 Deg C, 2) room temperature, 3) 48 h.; | 86% |
With dimethylsulfide; ozone 1.) methylene chloride, -78 deg C, 2.) room temperature, 3 h; Multistep reaction; |
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 24h; Title compound not separated from byproducts.; | A 85% B 15% |
{IrH2(acetone)2(PPh3)2}SbF6
1-methylcyclopent-1-ene
hydrido(η-methylcyclopentadienyl)bis(triphenylphosphine)iridium(III) hexafluoroantimonate
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene refluxed for 6 h under inert atmosphere; cooled, evapd., residue recrystd. from CH2Cl2-Et2O; | 85% |
1-methylcyclopent-1-ene
(C5(CH3)5)Y(η(3)-C5H6CH3)
Conditions | Yield |
---|---|
In further solvent(s) under inert atm. using Schlenk techniques; 1-methylcyclopentene added to((C5Me5)YH)2 dissolved in C6D11CD3 at -196°C; mixt. warmed to 0. degree.C; monitored by NMR (about 4 h); | 85% |
Conditions | Yield |
---|---|
In diethyl ether for 8h; Cycloaddition; Heating; | 84.7% |
methanol
1-methylcyclopent-1-ene
A
7-Methoxy-7-methyl-1,2-dioxepan-3-ol
C
1-hydroperoxy-1-methoxy-5-oxo-hexane
Conditions | Yield |
---|---|
With ozone at -78℃; Yields of byproduct given; | A 84% B n/a C n/a |
With ozone at -78℃; Yield given. Title compound not separated from byproducts; | A 84% B n/a C n/a |
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