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TIANFUCHEM--1066-45-1---TRIMETHYLTIN CHLORIDE Application:TIANFUCHEM--1066-45-1---TRIMETHYLTIN CHLORIDE
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Conditions | Yield |
---|---|
With tin(IV) chloride at -20 - 60℃; for 16h; Inert atmosphere; | 100% |
With hydrogenchloride In chloroform 4h boiling, under inflow of gaseous HCl; | 70% |
With HCl In chloroform 4h boiling, under inflow of gaseous HCl; | 70% |
trimethyl(dimesylamino)stannane
benzoyl chloride
A
trimethyltin(IV)chloride
B
N,N-bis(methanesulfonyl)benzamide
Conditions | Yield |
---|---|
In dichloromethane reflux for 48 h; evapn. of solvent, pptn. of N-benzoyldimesylamine, isolation of (CH3)3SnCl from filtrate; | A 100% B n/a |
trimethyl(dimesylamino)stannane
benzoyl chloride
A
trimethyltin(IV)chloride
B
N,N-bis(methanesulfonyl)benzamide
Conditions | Yield |
---|---|
In dichloromethane reflux for 48 h; evapn. of solvent, pptn. of N-benzoyldimesylamine, isolation of (CH3)3SnCl from filtrate; | A 100% B n/a |
Conditions | Yield |
---|---|
With triphenylphosphine In ethanol; acetone byproducts: Ni, triphenylphosphonium sulfide; dropwise addn. of an ethanolic soln. of NiCl2*6H2O to a stirred soln. of ((CH3)3Sn)2S and triphenylphosphine in acetone; refluxing;; filtration;; | 100% |
Conditions | Yield |
---|---|
stirring overnight at 60°F, N2-atmosphere; distd. at 15 Torr; | 99% |
molar ratio of (CH3)4Sn:SnCl4=3:1; distn.; | |
In neat (no solvent) react. Me4Sn with SnCl4 (3:1) at 130°C for 2 h; recrystn. from hexane; |
tetramethylstannane
phenyltin trichloride
A
trimethyltin(IV)chloride
B
methylphenyltin(IV) dichloride
Conditions | Yield |
---|---|
equimolar amts. of educts, 0°C, 1.5h; | A 99% B 85% |
equimolar amts. of educts, 0°C, 1.5h; | A 99% B 85% |
Conditions | Yield |
---|---|
In benzene-d6 byproducts: germanium-contg. polymer; (Ar); stirring (20°C, 2 d); | 99% |
Conditions | Yield |
---|---|
In water; acetone dropwise addn. of an aq. soln. of NiCl2*6H2O to a stirred soln. of ((CH3)3Sn)2S in acetone at room temp.; refluxing for 5 h;; filtration;; | A 90% B 99% |
O,O-dimethylphosphorylsulfenyl chloride
trimethyl(allyl)stannane
A
S-allyl O,O-dimethyl phosphorothioate
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In tetrachloromethane from -15 deg C to RT; | A 97% B n/a |
In tetrachloromethane addn. of soln. of sulfenyl chloride to soln. of stannane in CCl4 with cooling (-15°C) and stirring, warming to room temp.; solvent removed, distilln., (1)H-NMR; | A 97% B n/a |
(4-methoxyphenyl)trimethylstannane
N-methyl-N-phenylformamide
A
trimethyltin(IV)chloride
B
4-methoxy-benzaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate at 50 - 70℃; for 3h; | A n/a B 96% |
tetramethylstannane
butyl-methyl-tin dichloride
A
trimethyltin(IV)chloride
B
butyl-dimethyl-tin chloride
Conditions | Yield |
---|---|
3h, 75 to 85°C; | A 96% B 91% |
3h, 75 to 85°C; | A 96% B 91% |
bis(triphenylphosphine)nickel(II) chloride
bis(trimethyltin) sulfide
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In ethanol byproducts: Ni, triphenylphosphonium sulfide, triphenylphosphine; a mixt. of ((CH3)3Sn)2S and ((C6H5)3P)2NiCl2 in ethanol was heated at 95-100°C for 10 h;; distn.;; | 95% |
bis(trimethylstannyl)methane
dimethyltin dichloride
A
bis(chlorodimethylstannyl)methane
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In neat (no solvent) heated at 60°C for 12 h; distd. (12-15 Torr), recrystd. (C6H6); elem. anal.; | A 95% B n/a |
2,2-bis(trimethylstannyl)propane
dimethyltin dichloride
A
2,2-bis(chlorodimethylstannyl)propane
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In neat (no solvent) 2,2-bis(trimethylstannyl)propane placed in flash with 2 mol of dimethyldichlorostannane, heated at 60°C overnight; stirred at 15-20 Torr, warmed at 0.01 Torr to 100°C, recrystd. (CCl4); elem. anal.; | A 95% B n/a |
3,3-bis(trimethylstannyl)propyl ethyl sulfoxide
dimethyltin dichloride
3,3-bis(chlorodimethylstannyl)propyl ethyl sulfoxide
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In dichloromethane mixt. of the sulfoxide (6.7 mmol) and SnMe2Cl2 (13.5 mmol) in CH2Cl2 refluxed for 12 h; solvent removed (rotary evaporator); SnMe3Cl removed (0.01 torr, 60 °C); recrystn. (CCl4/hexane); elem. anal.; mol. wt. calc.: 486.6; mol. wt. found: 506.6 (isopiestic in CH2Cl2 at 22 °C); | A 95% B n/a |
chloro-trimethyl-silane
trimethyl(trifluoro-1-propynyl)stanane
A
1,1,1-trifluoro-3-trimethylsilyl-2-propyne
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In N,N,N,N,N,N-hexamethylphosphoric triamide mixt. heating (80°C, 0.5 h); Si-compd. isolation (vac. distn., elem. anal., IR and NMR spectroscopy); | A 92% B n/a |
di-tert-butyltin dichloride
tris(trimethylstannyl)amine
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In dichloromethane (inert atmosphere); stirring (-78°C to room temp.); removal of CH2Cl2 and trapping Me3SnCl at -78°C by applying high vacuum, NMR monitoring; | A 0% B 92% |
tetramethylstannane
Ethylbutylzinndichlorid
A
trimethyltin(IV)chloride
B
n-Butyl-ethylmethyl-zinnchlorid
Conditions | Yield |
---|---|
4h, 120 to 130°C; | A 91% B 76% |
4h, 120 to 130°C; | A 91% B 76% |
trimethylphenoxystannane
methanesulfonyl chloride
A
phenyl methanesulfonate
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In tetrachloromethane Kinetics; Me3SnOPh refluxed for 5 h with MeSO2Cl in CCl4 / kinetics measured at 120-150°C; Me3SnCl not isolated; detected by NMR; | A 91% B n/a |
In further solvent(s) Kinetics; educts dissolved in CH2Br2, sealed in glass tube, heated at 120-140°C; NMR anal.; | |
In dichloromethane Kinetics; educts dissolved in CH2Cl2, sealed in glass tube, heated at 130-160°C; NMR anal.; | |
In benzonitrile Kinetics; educts dissolved in PhCN, sealed in glass tube, heated at 120-140°C; NMR anal.; | |
In acetonitrile Kinetics; educts dissolved in MeCN, sealed in glass tube, heated at 100-130°C; NMR anal.; |
O,O-dimethylphosphorylsulfenyl chloride
p-vinylbenzyltrimethylstannane
A
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In diethyl ether addn. of P-compound in soln. to stirred soln. of stannane at -50-70°C; solvent removed, (CH3)3SnCl isolated, extn. with ether (5 times), solvent removed; elem. anal.; | A 91% B 87% |
In chloroform addn. of P-compound in soln. to stirred soln. of stannane at -20-30°C over 0.5h; solvent removed, (CH3)3SnCl isolated, chromy. (silica gel, Rf 0.07, benzene:acetone 4:1); elem. anal.; | A 48% B 35% |
In tetrachloromethane soln. of equimolar amts. of starting materials mixed at -20 and 20°C; not isolated, detd. by H-NMR; | |
In benzene-d6 soln. of equimolar amts. of starting materials or with stannane to sulfenyl ratio of 2:1 mixed at 10°C; not isolated, detd. by H-NMR; |
trimethyl(trimethylstannanylethynyl)silane
A
1,4-bis(trimethylsilyl)-1,3-butadiyne
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
With iron(III) chloride In tetrachloromethane; toluene at 25℃; for 1.5h; | A 90% B 90% |
With iron(III) chloride In tetrachloromethane; cyclohexane byproducts: FeCl2; at 25°C for 1.5 h; | A 90% B n/a |
hydrogenchloride
trimethyl(dimesylamino)stannane
A
dimesylamine
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In dichloromethane stream of HCl for 3 h, stirring for 1 h at 20°C; pptn. of dimesylamine, filtration, isolation of (CH3)3SnCl from filtrate; | A n/a B 90% |
hydrogenchloride
trimethyl(dimesylamino)stannane
A
dimesylamine
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In dichloromethane stream of HCl for 3 h, stirring for 1 h at 20°C; pptn. of dimesylamine, filtration, isolation of (CH3)3SnCl from filtrate; | A n/a B 90% |
SiF3SiHCl2
trimethylstannane
A
F3SiSiH3
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
In neat (no solvent) Warming of starting materials (in absence of solvent, vac. line) for 30 min to room temp.; Removal of Me3SnCl by passing the mixt. through a trap cooled to -95°C (toluene), IR and NMR identification of volatile resulting compd.; | A 90% B n/a |
In neat (no solvent) Condensing of 1 equiv. of Si-compd. with 2 equiv. of Me3SnH at -196°C (vac. line, no solvent). React. is obsd. via F-NMR only after warming (0°C, 30 min), while at -10°C (25 min) no react. occurs.; After 1 h at 0°C peaks due to SiF3SiH2Cl and unreacted SiF3SiHCl2 disappear and Me3SnCl is removed by passing the mixt. through a trap cooled to -95°C (toluene).; | A 90% B n/a |
Conditions | Yield |
---|---|
In dichloromethane stoichiometric ratio, stirring (8 h, room temp.); evapn. (vac.), washing (n-hexane, toluene), drying (vac.); elem. anal.; | A 89.5% B n/a |
In toluene stoichiometric ratio, stirring (5 d, room temp.); filtn., evapn. (vac.), washing (n-hexane), drying (vac.); | A 86% B n/a |
1-trimethylsilyl-2-phenyl-2-trimethylstannyl-ethene
A
1-trimethylsilyl-2-phenyl-2-chloromercuri-ethene
B
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
With potassium fluoride In tetrahydrofuran Solid HgCl2 is added to a soln. of the ethene-compd. in THF at room temp. After 20 h stirring KF is added.; After filtn. and removal of the solvent the residue is sublimed at 80°C/10-E2 torr, giving a highly viscous oil; elem. anal.; | A 89% B n/a |
1,1,1,2,2,3,3-heptafluoro-3-iodo-propane
(3,3-dimethyl-1-butynyl)trimethylstannane
A
2,2,7,7-tetramethyl-octa-3,5-diyne
B
trimethyltin(IV)chloride
C
5,5,6,6,7,7,7-heptafluoro-2,2-dimethyl-3-heptyne
D
trimethylstannyl iodide
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In 1,2-dichloro-ethane 100°C, 3 h, sealed glass ampul purged with argon; 0.5 M Me3SnCCBu-t, 1 M C3F7I, catalyst concn. 1 mol % of the amount of Me3SnCCBu-t; | A 2-3 B <=2 C 88% D n/a |
bis-triphenylphosphine-palladium(II) chloride In 1,2-dichloro-ethane 100°C, 3 h, sealed glass ampul purged with argon; 0.5 M Me3SnCCBu-t, 1 M C3F7I, catalyst concn. 1 mol % of the amount of Me3SnCCBu-t; | A 2-3 B <=2 C 87% D n/a |
bis(benzonitrile)palladium(II) dichloride In 1,2-dichloro-ethane 100°C, 3 h, sealed glass ampul purged with argon; 0.5 M Me3SnCCBu-t, 1 M C3F7I, catalyst concn. 1 mol % of the amount of Me3SnCCBu-t; | A 2-3 B <=2 C 70% D n/a |
Conditions | Yield |
---|---|
In dichloromethane stoichiometric ratio, stirring (8 h, room temp.); evapn. (vac.), washing (n-hexane, toluene), drying (vac.); elem. anal.; | A 88% B n/a |
In toluene stoichiometric ratio, stirring (5 d, room temp.); filtn., evapn. (vac.), washing (n-hexane), drying (vac.); | A 80% B n/a |
trimethyltin(IV)chloride
sodium
4-methoxy-N,N,N-trimethylbenzenaminium iodide
(4-methoxyphenyl)trimethylstannane
Conditions | Yield |
---|---|
With methyl iodide In ammonia Irradiation (UV/VIS); condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of CH3OC6H4NMe3I; irradn. with stirring for30 min, quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether; | 100% |
With para-dinitrobenzene; methyl iodide In ammonia Irradiation (UV/VIS); condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of p-dinitrobenzene and then addn. of CH3OC6H4NMe3I; irradn. with stirring for 30 min, quenching by addn. of MeI inexcess; evapn. of ammonia, treatment with water, extn. with ether; | 34% |
With methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, then addn. of CH3OC6H4NMe3I; holding in dark for 30 min; quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether; | 14% |
With para-dinitrobenzene; methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of p-dinitrobenzene and then addn. of CH3OC6H4NMe3I, holding in dark for 30 min, quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether; | 0% |
1,2-dimethoxybenzene
trimethyltin(IV)chloride
(2,3-dimethoxyphenyl)trimethylstannane
Conditions | Yield |
---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane BuLi in hexane added to stirred soln. of veratrole and TMEDA in Et2O at 0°C, warmed to 22°C, stirred 1h, cooled to -80°C, addn. of (CH3)3SnCl in Et2O, warmed to 22°C, after 90 min H2O was added, stirred (room temp. overnight); Et2O layer washed with water, dried (Na2SO4), filtered, concentrated under reduced pressure, distn. (Kugelrohr, 110°C, 0.04 mmHg); elem. anal.;; | 100% |
1,5-dihydro-s-indacene
trimethyltin(IV)chloride
1-(trimethylstannyl)-1,5-dihydro-s-indacene
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane byproducts: LiCl; To a soln. of s-indacene in THF at -78°C n-BuLi in hexane was added, mixt. allowed to warm slowly to 5-10°C; this soln. was added to a soln. of Me3SnCl in hexane;; LiCl was filtered; solvent was removed in vac., oil was crystd. on standing; elem. anal.;; | 100% |
2,2'-Bithiophene
trimethyltin(IV)chloride
5,5'-bis(trimethylstannyl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -40 - 25℃; for 2h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -40 - 25℃; for 3h; | 100% |
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -40 - 20℃; for 0.583333h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane Inert atmosphere; | 93% |
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; for 1h; | 90% |
trimethyltin(IV)chloride
sodium
(4-cyanophenyl)trimethylammonium iodide
(4-cyanophenyl)trimethylstannane
Conditions | Yield |
---|---|
With methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, then addn. of CNC6H4NMe3I; holding in dark for 0.08 h; quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether; | 100% |
With methyl iodide In ammonia Irradiation (UV/VIS); condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of CNC6H4NMe3I; irradn. with stirring for 0.08 h, quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether; | 100% |
With para-dinitrobenzene; methyl iodide In ammonia condensation of sodium-dried ammonia into round-bottomed Pyrex flask, addn. of Me3SnCl and Na, addn. of p-dinitrobenzene and then addn. of CNC6H4NMe3I; holding in dark for 0.08 h; quenching by addn. of MeI in excess; evapn. of ammonia, treatment with water, extn. with ether; | 35% |
Conditions | Yield |
---|---|
In water byproducts: KCl; | 100% |
3-(tetrahydropyran-2'-yloxy)propyne
trimethyltin(IV)chloride
2-(1-trimethylstannyl-3-propynyloxy) tetrahydropyran
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane (Ar); soln. of n-BuLi in hexane was added dropwise to soln. of alkyne inTHF at -78°C; mixt. was stirred at -78°C for 30 min; Sn c ompd. was added; mixt. was stirred for 30 min and slowly warmed from -78°C to -30°C; extd. (ether/H2O); aq. phase washed (ether); combined org. phase dried (MgSO4); filtered; concd.; | 100% |
1-Bromo-2,4-dimethoxybenzene
trimethyltin(IV)chloride
(2,4-dimethoxyphenyl)trimethylstannane
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran aryl halide added to stirred suspn. of Mg turnings in THF (under N2), heated at reflux for 90 min, cooled to room temp., addn. of (CH3)3SnCl, stirred at room temp. for 2h;; partitioned between Et2O and H2O, aq. phase extd. with Et2O, organic phase washed with H2O, dried (MgSO4), filtered, concentrated under reduced pressure, filtered through deep pad of silica (THF/hexane (1:19)); elem. anal.;; | 100% |
benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene
trimethyltin(IV)chloride
2,5,8-tris(trimethylstannyl)benzo[1,2-b:3,4-b’:5,6-b’’]trithiophene
Conditions | Yield |
---|---|
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene In tetrahydrofuran; hexane at 0 - 20℃; for 6h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere; | 100% |
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Schlenk technique; | 94% |
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere; Reflux; | 82% |
Stage #1: benzo(1,2-b;3,4-b′;5,6-b′′)trithiophene With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at 0℃; Inert atmosphere; | 75% |
trimethyltin(IV)chloride
4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole
4,7-bis(5-(trimethylstannyl)thiophene-2-yl)benzo[c][1,2,5]thiadiazole
Conditions | Yield |
---|---|
Stage #1: 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole With 2,2,6,6-tetramethylpiperidinyl-lithium Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; | 100% |
Stage #1: 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃; for 12h; | 89% |
Stage #1: 4,7-bis(thiophen-2-yl)-2,1,3-benzothiadiazole With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78℃; | 85% |
Conditions | Yield |
---|---|
Stage #1: toluene With (-)-sparteine at -78℃; Stage #2: With n-butyllithium at -78 - 20℃; for 0.5h; Stage #3: trimethyltin(IV)chloride at -78℃; for 2h; | 100% |
Conditions | Yield |
---|---|
Stage #1: C21H24O2S3 With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere; | 100% |
2-(2-ethylhexyl)thiophen
trimethyltin(IV)chloride
(5-(2-ethylhexyl)thiophen-2-yl)trimethylstannane
Conditions | Yield |
---|---|
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Schlenk technique; | 100% |
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; Inert atmosphere; | 86.5% |
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃; | |
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 2h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at -78 - 20℃; | |
Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 0.68 g |
3-hexylthiophene
trimethyltin(IV)chloride
(3-hexylthiophene-5-yl)trimethylstannane
Conditions | Yield |
---|---|
Stage #1: 3-hexylthiophene With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 1h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; for 14h; | 100% |
Stage #1: 3-hexylthiophene With lithium diisopropyl amide Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78℃; | 98% |
Stage #1: 3-hexylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane for 1h; Reflux; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; diethyl ether; hexane at 0 - 20℃; for 2h; | 92% |
Stage #1: 3-hexylthiophene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 4h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 82.4% |
With lithium diisopropyl amide |
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
Stage #1: 7-bromo-N,N-bis(4-methoxyphenyl)-9,9-dimethyl-9H-fluoren-2-amine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - -20℃; Inert atmosphere; | 100% |
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
Stage #1: N,N-bis(4-methoxyphenyl)-4,4-dimethyl-4H-indeno[1,2-b]thiophen-6-amine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - -20℃; Inert atmosphere; | 100% |
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
Stage #1: 4,8-(1,12-dodecylenedioxy)benzo[1,2-b:4,5-b']dithiophene With n-butyllithium In tetrahydrofuran at 20℃; for 0.0333333h; Inert atmosphere; Glovebox; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran for 0.00277778h; Glovebox; | 100% |
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
Stage #1: 4-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-4H-dithieno[3,2-b:2',3'-d]pyrrole With n-butyllithium In tetrahydrofuran at -78 - 5℃; for 3h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78℃; for 5h; | 100% |
2-(3,4,5-tris(dodecyloxy)phenyl)thiophene
trimethyltin(IV)chloride
2-(3,4,5-tridodecyloxyphenyl)-5-trimethylstannylthiophene
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -40℃; | 100% |
trimethyltin(IV)chloride
5′-hexyl-2,2′-bithiophene-5-trimethylstannane
Conditions | Yield |
---|---|
Stage #1: 2-hexylthieno[3,2-b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane at 20℃; | 100% |
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-(4,5-dibutoxy-2-(5-phenylthiophen-2-yl)phenyl)thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; hexane | 100% |
2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane
trimethyltin(IV)chloride
Conditions | Yield |
---|---|
Stage #1: 2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane With n-butyllithium In tetrahydrofuran; water at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; water at -78 - 20℃; Inert atmosphere; | 99.9% |
Stage #1: 2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 99.8% |
2-(2'-butyl-1'-octyl)thiophene
trimethyltin(IV)chloride
2-(2-butyloctyl)-5-trimethylstannylthiophen
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran | 99.2% |
trimethyltin(IV)chloride
(S)-2-(2-Methylbutyl)thiophene
(S)-2-(2-methylbutyl)-5-trimethylstannylthiophene
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran | 99.1% |
trimethyltin(IV)chloride
1-tert-butyldimethylsilyl-3-trimethylstannyl-7-azaindole
Conditions | Yield |
---|---|
Stage #1: 3-bromo-1-(tert-butyldimethylsilyl)-1H-pyrrolo[2,3-b]pyridine With tert.-butyl lithium In tetrahydrofuran; pentane at -90℃; for 0.0833333h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran; diethyl ether; pentane at -90℃; for 1h; | 99% |