Conditions | Yield |
---|---|
With n-butyllithium In pentane for 2.5h; Inert atmosphere; Glovebox; | 87% |
With n-butyllithium In hexane at 21℃; for 2h; | 84% |
With phenyllithium |
Conditions | Yield |
---|---|
With lithium; zinc(II) chloride; 2,5-Diphenyl-6a-thiathiophthen In tetrahydrofuran at 0℃; under 750.06 Torr; for 6h; Product distribution; | A 75% B n/a |
With lithium; 2,5-Diphenyl-6a-thiathiophthen; zinc(II) chloride In tetrahydrofuran at 0℃; under 750.06 Torr; for 6h; Yields of byproduct given; | A 75% B n/a |
Conditions | Yield |
---|---|
With lithium | |
With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2h; |
Conditions | Yield |
---|---|
With lithium |
Conditions | Yield |
---|---|
With diethyl ether | |
Ambient temperature; |
1,1-Dilithioethan
vinyllithium
Conditions | Yield |
---|---|
With chloro-trimethyl-silane In tetrahydrofuran for 8h; Ambient temperature; Yield given; |
1,2-dilithioethane
vinyllithium
1,2-dilithioethane
A
vinyllithium
B
1,4-dilithiobutane
C
hexanediyl dilithium
Conditions | Yield |
---|---|
With lithium at -196℃; under 0.005 Torr; Mechanism; |
cis-1,2-Dilithioethylen
A
vinyllithium
B
dilithium acetylide
Conditions | Yield |
---|---|
Title compound not separated from byproducts; |
trans-1,2-Dilithioethylen
A
vinyllithium
B
dilithium acetylide
Conditions | Yield |
---|---|
Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With dilithiumethylene Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane at 0℃; for 0.5h; | |
In tetrahydrofuran; hexane at -78 - 20℃; for 1.08333h; | |
In pentane Inert atmosphere; | |
In hexane at 20℃; for 1h; |
Conditions | Yield |
---|---|
In diethyl ether at 0℃; for 0.5h; Inert atmosphere; |
Conditions | Yield |
---|---|
With n-butyllithium In pentane at -78℃; Inert atmosphere; |
Conditions | Yield |
---|---|
In tetrahydrofuran -78 deg C to room temp.; | 100% |
vinyllithium
2-methyl-6-methylenetricyclo<3.3.1.02,7>nonan-8-one
8-ethenyl-2-methyl-6-methylenetricyclo<3.3.1.02,7>nonan-8-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 1.5h; | 100% |
vinyllithium
(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone
Conditions | Yield |
---|---|
Stage #1: vinyllithium With copper(l) cyanide In diethyl ether at -78 - 0℃; Stage #2: (4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone In diethyl ether at -78℃; for 0.25h; Stage #3: With ammonium chloride In water | 100% |
dichloro(η(5)-1-[2-(N,N-dimethylamino)ethyl]-2,3,4,5-tetramethylcyclopentandienyl)(η(5)-pentamethylcyclopentadienyl)titanium
vinyllithium
(η(5)-1-[2-(N,N-dimethylamino)ethyl]-2,3,4,5-tetramethylcyclopentandienyl)(η(5)-pentamethylcyclopentadienyl)(2-methylidene)titanacyclobutane
Conditions | Yield |
---|---|
In tetrahydrofuran N2-atmosphere; -78°C to room temp.; evapn., extg. (hexane), filtering, evapn.; | 100% |
(2RS,4SR,5RS)-2,5-diphenyl-3,4-dimethyl-1,3,2-oxazaphospholidine-2-borane
vinyllithium
(RSp)-(N-methyl[(1RS,2SR)-(1-hydroxy-1-phenylprop-2-yl)]amino)phenyl-(vinyl)phosphine borane
Conditions | Yield |
---|---|
In tetrahydrofuran (Ar); soln. of Li compd. in THF was added dropwise to soln. of B-P compd. in THF at -78°C; mixt. was stirred at -78°C for 30 min; warmed to room temp.; H2O added; THF removed (vac.); extd. (CH2Cl2); dried (MgSO4); solvent evapd; chromd. (silica gel, toluene/EtOAc, 9/1); | 100% |
vinyllithium
(E)-4-methoxy-N-(naphthalene-1-ylmethylene)phenylamine
(4-Methoxy-phenyl)-(1-naphthalen-1-yl-allyl)-amine
Conditions | Yield |
---|---|
1-(2-methoxyphenoxy)-N,N-dimethyl-3-phenylpropan-2-amine In toluene at -42℃; | 99% |
vinyllithium
5-Methyl-5-(phenylthio)-2-hexanone
Conditions | Yield |
---|---|
In diethyl ether at -78 - -20℃; for 2.5h; | 98% |
vinyllithium
(1aR,3S,3aR,3bS,5aR,6S,8aR,8bR,10R,10aR)-6-((S)-1-Hydroxy-1-methyl-allyl)-10-methoxy-3,8a-bis-methoxymethoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 1h; | 97% |
vinyllithium
6-Methyl-6-(2-trimethylsilanylmethyl-allyl)-cyclohex-2-enone
(1S,6R)-6-Methyl-6-(2-trimethylsilanylmethyl-allyl)-1-vinyl-cyclohex-2-enol
Conditions | Yield |
---|---|
97% |
vinyllithium
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 0.25h; | 97% |
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 0.5h; | 97% |
vinyllithium
[4-(benzylideneamino)phenyl]methanol
N-(p-methoxyphenyl)-α-ethenylbenzenemethaneamine
Conditions | Yield |
---|---|
1-(2-methoxyphenoxy)-N,N-dimethyl-3-phenylpropan-2-amine In toluene at -42℃; | 96% |
vinyllithium
4-(t-butyldimethylsilyloxy)-3-methoxycyclopent-2-enone
5-(tert-Butyl-dimethyl-silanyloxy)-3-vinyl-cyclopent-2-enone
Conditions | Yield |
---|---|
In diethyl ether at -78 - -20℃; for 1h; | 96% |
vinyllithium
Acetic acid (1R,2R,4S,5R,6S,8S)-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-11-methylene-10-oxo-12-oxa-tricyclo[6.3.1.01,6]dodec-4-yl ester
Acetic acid (1R,2R,4S,5R,6S,8S,11S)-11-allyl-5-benzyloxy-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-oxo-12-oxa-tricyclo[6.3.1.01,6]dodec-4-yl ester
Conditions | Yield |
---|---|
With CuCN In diethyl ether at -60℃; Addition; | 96% |
vinyllithium
6-methyl-6-(phenylthio)hept-1-en-3-ol
Conditions | Yield |
---|---|
In diethyl ether at -78 - -20℃; for 2.5h; | 96% |
vinyllithium
dimethyl (S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate
dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate
Conditions | Yield |
---|---|
Stage #1: vinyllithium With copper(l) iodide In diethyl ether at -78 - -35℃; for 0.333333h; Stage #2: dimethyl (S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate In diethyl ether at -78 - -30℃; for 1h; Michael addition; Further stages.; | 96% |
2-Benzenesulfonyl-6-benzyloxy-6-methyl-7-oxa-bicyclo[2.2.1]hept-2-ene
vinyllithium
(1R,2R,5R)-3-Benzenesulfonyl-5-benzyloxy-5-methyl-2-vinyl-cyclohex-3-enol
Conditions | Yield |
---|---|
In toluene at -78℃; | 95% |
vinyllithium
2(R)-(Z)-propenyl-(3,5-dideoxy-1,2-O-isopropylidene-α-D-ribo-furano)<3,4-c>cyclohexanone
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - 20℃; | 95% |
vinyllithium
Conditions | Yield |
---|---|
In toluene at -78℃; for 0.25h; | 95% |
vinyllithium
dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate
dimethyl (2R,3S,5R,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-3-vinylpiperidine-1,2-dicarboxylate
Conditions | Yield |
---|---|
Stage #1: vinyllithium With copper(l) iodide In diethyl ether at -78 - -35℃; for 0.333333h; Stage #2: dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate In diethyl ether at -78 - -20℃; for 1h; Michael addition; Further stages.; | 95% |
iron(II)(carbonyl)2(trimethylphosphine)2Br2
vinyllithium
cis,trans-Fe(CO)2(PMe3)2(CH=CH2)Br
Conditions | Yield |
---|---|
In diethyl ether under N2 atm. to soln. cis,trans,cis-Fe(CO)2(PMe3)2Br2 in Et2O soln. CH2=CHLi in Et2O was added dropwise, 10 min; soln. was washed with water, Et2O phase was dried over MgSO4, crystn. from n-hexane at -20°C; | 95% |
vinyllithium
3-methoxy-6,6-dimethyl-2-[4-(1-methylethyl)-2,3,5-trimethoxyphenylmethyl]-2-cyclohexenone
3-ethenyl-4,4-dimethyl-2-[4-(1-methylethyl)-2,3,5-trimethoxyphenylmethyl]-2-cyclohexenone
Conditions | Yield |
---|---|
Acidic aq. solution; | 95% |
Stage #1: vinyllithium; 3-methoxy-6,6-dimethyl-2-[4-(1-methylethyl)-2,3,5-trimethoxyphenylmethyl]-2-cyclohexenone Inert atmosphere; Stage #2: Inert atmosphere; Acidic conditions; | 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran at -55℃; | 94% |
vinyllithium
N-phenyl-N'-((trimethylsilyl)methyl)carbodiimide
N-Phenyl-N'-trimethylsilanylmethyl-acrylamidine
Conditions | Yield |
---|---|
In tetrahydrofuran for 1h; | 94% |
vinyllithium
6,7-dihydrocyclopenta[d][1,3]dioxin-5(4H)-one
2-(hydroxymethyl)-3-vinyl-2-cyclopentenone
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 0.25h; | 94% |
vinyllithium
2-[(benzyloxy)methyl]cyclohex-2-en-1-one
2-Benzyloxymethyl-1-vinyl-cyclohex-2-enol
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; | 94% |
vinyllithium
1-<4'-(S)-tert-butyloxazolin-2'-yl>naphthalene
methyl iodide
(S)-4-tert-Butyl-2-((1S,2S)-1-methyl-2-vinyl-1,2-dihydro-naphthalen-1-yl)-4,5-dihydro-oxazole
Conditions | Yield |
---|---|
at 0℃; for 36h; | 94% |
Product distribution; Mechanism; various times and temperatures; other organolithium compounds; |
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - 0℃; for 0.5h; | 94% |
In tetrahydrofuran Ring cleavage; substitution; | 94% |
vinyllithium
3-methyl-3-(phenylthio)butanal
5-methyl-5-(phenylthio)hex-1-en-3-ol
Conditions | Yield |
---|---|
In diethyl ether at -78 - -20℃; for 2.5h; | 94% |
vinyllithium
6-methyl-5-(phenylthio)hept-5-en-2-one
3,7-dimethyl-6-(phenylthio)octa-1,6-dien-3-ol
Conditions | Yield |
---|---|
In diethyl ether at -78 - -20℃; for 2.5h; | 94% |
Product Name: Vinyllithium (CAS NO.917-57-7)
Molecular Formula: C2H3Li
Molecular Weight: 33.99g/mol
Mol File: 917-57-7.mol
Einecs: 213-028-5
Enthalpy of Vaporization: 15.7 kJ/mol
Vapour Pressure: 43300 mmHg at 25°C
H-Bond Donor: 0
H-Bond Acceptor: 1
Heavy Atom Count: 3
Complexity: 2.8
Covalently-Bonded Unit Count: 2
Ignites spontaneously and burns violently in air. See also LITHIUM COMPOUNDS and ORGANOMETALS.
Vinyllithium ,its CAS NO. is 917-57-7,the synonyms is Ethenyllithium .
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