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Conditions | Yield |
---|---|
In not given tin compd. was recovered at room temp. under vac.; | A n/a B 100% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In dichloromethane at room temp. for 23 h; | 98% |
Conditions | Yield |
---|---|
In diethyl ether excess of CH3OH; | 97% |
carbonic acid dimethyl ester
bis(tri-n-butyltin)oxide
tributyltin methoxide
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: CO2; 130-135°C; 40 min; reflux; | 96% |
at 90℃; for 18h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With methanesulfonic acid In dichloromethane at room temp. for 16 h; | 87% |
With trifluorormethanesulfonic acid In dichloromethane at room temp. for 16 h; | 82% |
With trifluoroacetic acid In dichloromethane at room temp. for 16 h; | 65% |
Conditions | Yield |
---|---|
In toluene for 6h; Reflux; | 80% |
In methanol; toluene byproducts: NaCl; (Ar); Schlenk tube technique; Bu3SnCl in toluene was added dropwise to NaOCH3 in methanol; mixt. was refluxed for 6 h; NaCl was centrifuged; solvent was removed in vac.; residue was distd. under reduced pressure; elem. anal.; | 75% |
Conditions | Yield |
---|---|
In Petroleum ether excess of CH3OH; | 80% |
(C4H9)3SnOC5H8CH(CH3)COOCH3
A
ethylidenecyclopentane
B
tributyltin methoxide
C
cyclopentanone
Conditions | Yield |
---|---|
byproducts: (C4H9)3SnCH(CH3)COOCH3, CO2; 60 % decompn. at 180°C/5 Torr within 8 h; | A 72% B n/a C 28% |
byproducts: (C4H9)3SnCH(CH3)COOCH3, CO2; 60 % decompn. at 180°C/5 Torr within 8 h; | A 72% B n/a C 28% |
byproducts: (C4H9)3SnCH(CH3)COOCH3, CO2; 63 % decompn. at 200°C/5 Torr within 5 h; | A 68% B n/a C 32% |
byproducts: (C4H9)3SnCH(CH3)COOCH3, CO2; 63 % decompn. at 200°C/5 Torr within 5 h; | A 68% B n/a C 32% |
(C4H9)3SnOC6H10CH(CH3)COOCH3
A
ethylidenecyclohexane
B
tributyltin methoxide
C
cyclohexanone
D
methyl 2-(tributylstannyl)propionate
Conditions | Yield |
---|---|
byproducts: CO2; 52 % decompn. at 150°C/0.8 Torr for 8 h; | A 71% B n/a C 29% D n/a |
byproducts: CO2; 52 % decompn. at 150°C/0.8 Torr for 8 h; | A 71% B n/a C 29% D n/a |
byproducts: CO2; 52 % decompn. at 200°C/8 Torr for 4.5 h; | A 66% B n/a C 34% D n/a |
byproducts: CO2; 52 % decompn. at 200°C/8 Torr for 4.5 h; | A 66% B n/a C 34% D n/a |
methanol
tributyltin chloride
sodium methylate
tributyltin methoxide
Conditions | Yield |
---|---|
With methanol In methanol byproducts: CH3COC3H7; Irradiation (UV/VIS); |
Conditions | Yield |
---|---|
In methanol Irradiation (UV/VIS); |
methanol
tri-n-butyl-tin hydride
1-Phenyl-1-(tri-n-butylstannyloxy)-propen
B
tributyltin methoxide
Conditions | Yield |
---|---|
In methanol Irradiation (UV/VIS); |
methanol
(C6H5)3SnOC(C6H5)CHCH3
tri-n-butyl-tin hydride
B
tributyltin methoxide
Conditions | Yield |
---|---|
In methanol Irradiation (UV/VIS); |
1.1.1-Tribrom-2.2-bis--ethan
A
tributyltin methoxide
B
tributyltin formate
Conditions | Yield |
---|---|
With methanol at 33°C, 2 h; | |
With CH3OH at 33°C, 2 h; |
1.1.1-Trichlor-2.2-bis--ethan
A
tributyltin methoxide
B
tributyltin formate
Conditions | Yield |
---|---|
With methanol at 55°C, 6 h or at 33°C, 66 h; | |
With CH3OH at 55°C, 6 h or at 33°C, 66 h; |
Conditions | Yield |
---|---|
With acetylene In methanol byproducts: olefine; reaction at 150-155°C;; | |
With olefine In methanol byproducts: alkane; reaction at 150-155°C;; |
(C4H9)3SnOC(OCH3)NSO2C6H5
di-n-propylamine
tributyltin methoxide
Conditions | Yield |
---|---|
byproducts: C6H5NHCON(C3H7)2; | |
byproducts: C6H5NHCON(C3H7)2; |
tributyl-tribromomethyl-stannane
tributyltin methoxide
Conditions | Yield |
---|---|
With methanol In methanol byproducts: CHBr3; | |
With CH3OH In methanol byproducts: CHBr3; |
3-methyl-2-(tributylstannyl)butanenitrile
tributyltin methoxide
Conditions | Yield |
---|---|
With CH3OH In methanol byproducts: (CH3)2CHCH2CN; refluxing;; |
<1-Aethoxycarbonyl-2-methylpropyl-(1)>-tributylzinn
tributyltin methoxide
Conditions | Yield |
---|---|
With CH3OH In methanol byproducts: (CH3)2CHCH2COOC2H5; refluxing;; |
1.1.1.3.3.3-Hexachlor-2-methoxy-2--propan
tributyltin methoxide
Conditions | Yield |
---|---|
With methanol byproducts: CCl3COOCH3, CHCl3; at 33°C for 2-3 h; | |
With CH3OH byproducts: CCl3COOCH3, CHCl3; at 33°C for 2-3 h; |
(C4H9)3SnOC(C6H5)2CH(CH3)COOCH3
A
benzophenone
B
1,1-diphenyl-1-propene
C
tributyltin methoxide
D
methyl 2-(tributylstannyl)propionate
Conditions | Yield |
---|---|
byproducts: CO2; thermal decompn. at 160°C/0.3 Torr for 7 h or at 200°C/0.5 Torr for 0.75 h; ketone to olefin ratio = 62:38 or 65:35; | |
byproducts: CO2; thermal decompn. at 160°C/0.3 Torr for 7 h or at 200°C/0.5 Torr for 0.75 h; ketone to olefin ratio = 62:38 or 65:35; |
1.1.1-Tribrom-2-methoxy-2--ethan
tributyltin methoxide
Conditions | Yield |
---|---|
With methanol byproducts: HCOOCH3, CHBr3; at 55°C for 1 d or at 33°C for 3-4 d; | |
With CH3OH byproducts: HCOOCH3, CHBr3; at 55°C for 1 d or at 33°C for 3-4 d; |
(C4H9)3SnOC(C2H5)2CH(CH3)COOCH3
A
tributyltin methoxide
B
methyl 2-(tributylstannyl)propionate
Conditions | Yield |
---|---|
byproducts: CH3COC2H5, (C2H5)2CCHCH3, CO2; thermal decompn. at 180°C (10 Torr) for 2.5 h and at 200°C (30 Torr) for 1.5 h; | |
byproducts: CH3COC2H5, (C2H5)2CCHCH3, CO2; thermal decompn. at 180°C (10 Torr) for 2.5 h and at 200°C (30 Torr) for 1.5 h; |
(C4H9)3SnOC(CH3)(C3H7)CH(CH3)COOCH3
A
tributyltin methoxide
B
methyl 2-(tributylstannyl)propionate
Conditions | Yield |
---|---|
byproducts: CH3CO(i-C3H7), CH3(i-C3H7)CCHCH3, CO2; thermal decompn. at 200°C for 0.75 h; | |
byproducts: CH3CO(i-C3H7), CH3(i-C3H7)CCHCH3, CO2; thermal decompn. at 200°C for 0.75 h; |
(C4H9)3SnOC(CH3)(C6H5)CH(CH3)COOCH3
A
2-phenylbut-2-ene
B
tributyltin methoxide
C
acetophenone
D
methyl 2-(tributylstannyl)propionate
Conditions | Yield |
---|---|
byproducts: CO2; thermal decompn. at 160°C/0.3 Torr for 12 h or at 200°C/5 Torr for 3 h; ketone:olefin ratio = 79:21 or 72:28; | |
byproducts: CO2; thermal decompn. at 160°C/0.3 Torr for 12 h or at 200°C/5 Torr for 3 h; ketone:olefin ratio = 79:21 or 72:28; |
(C4H9)3SnOC(CH3)(C2H5)CH(CH3)COOCH3
A
tributyltin methoxide
B
methyl 2-(tributylstannyl)propionate
Conditions | Yield |
---|---|
byproducts: CH3COC2H5, CH3(C2H5)CCHCH3, CO2; thernal decompn. at 180°C for 2 h or at 200°C for 0.75 h; | |
byproducts: CH3COC2H5, CH3(C2H5)CCHCH3, CO2; thernal decompn. at 180°C for 2 h or at 200°C for 0.75 h; |
(C4H9)3SnOC(CH3)2CH(CH3)COOCH3
A
tributyltin methoxide
B
methyl 2-(tributylstannyl)propionate
Conditions | Yield |
---|---|
byproducts: CH3COCH3, (CH3)2CCHCH3, CO2; decompn. at 180°C for 6 h or at 200°C for 2 h; | |
byproducts: CH3COCH3, (CH3)2CCHCH3, CO2; decompn. at 180°C for 6 h or at 200°C for 2 h; |
β-1-bromo-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside
tributyltin methoxide
3,4,6-tri-O-benzoyl-1,2-O-[1-exo-(methoxy)benzylidene]-α-D-glucopyranoside
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In dichloromethane | 100% |
Conditions | Yield |
---|---|
In pentane -78°C; 3 h; | 100% |
In not given | 99.8% |
In not given | 99.8% |
Conditions | Yield |
---|---|
exothermic; | 100% |
In Petroleum ether 50 min; |
Conditions | Yield |
---|---|
In neat (no solvent) addn. of tributyltin alkoxide to aldehyde (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
In neat (no solvent) addn. of tributyltin alkoxide to aldehyde (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
1:1.1; | 85-100 |
Conditions | Yield |
---|---|
reflux; 4 h; | 100% |
1,1,1,3,3,3-hexachloro-propan-2-one
tributyltin methoxide
tributyl-trichloromethyl-stannane
Conditions | Yield |
---|---|
byproducts: CCl3COOCH3; 1:1.1; 33°C / 7 d and 55°C / 4 h; | 100% |
byproducts: Cl3CCOOCH3; 55°C, 4 h;; | |
byproducts: Cl3CCOOCH3; 55°C, 4 h;; |
1,1,1,3,3,3-hexachloro-propan-2-one
tributyltin methoxide
1.1.1.3.3.3-Hexachlor-2-methoxy-2--propan
Conditions | Yield |
---|---|
In tetrachloromethane 1:1; | 100% |
In neat (no solvent) addn. of tributyltin alkoxide to ketone (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
In neat (no solvent) addn. of tributyltin alkoxide to ketone (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
1,1,3-trichloro-1,3,3-trifluoroacetone
tributyltin methoxide
1.1.3-Trichlor-1.3.3-trifluor-2-methoxy-2--propan
Conditions | Yield |
---|---|
1:1.1; | 100% |
In neat (no solvent) addn. of tributyltin alkoxide to ketone (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
In neat (no solvent) addn. of tributyltin alkoxide to ketone (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) addn. of tributyltin alkoxide to aldehyde (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
In neat (no solvent) addn. of tributyltin alkoxide to aldehyde (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
1:1.1; | 85-100 |
Conditions | Yield |
---|---|
0°C; <1 min; | 100% |
tributyltin methoxide
2,4,6-tris(trimethylsiloxy)-1,3,5-triazine
1,3,5-tris-tributylstannanyl-[1,3,5]triazinane-2,4,6-trione
Conditions | Yield |
---|---|
150°C; | 100% |
Conditions | Yield |
---|---|
heating; | 100% |
perfluorobenzaldehyde
tributyltin methoxide
α-Methoxy-α--pentafluortoluol
Conditions | Yield |
---|---|
1:1.1; | 100% |
100% | |
100% |
Conditions | Yield |
---|---|
In Petroleum ether 1 h; | 100% |
In chloroform-d1 (Ar); Schlenk tube technique; tin compd. was dissolved in CDCl3; CO2 was admitted at room temp.; molar ratio CO2:Sn = 1; stirred under CO2 for 2 h; NMR monitoring; not isolated; | |
In tetrahydrofuran (Ar); Schlenk tube technique; tin compd. was dissolved in THF; CO2 was admitted at room temp. for 30 min; molar ratio CO2:Sn = 1; |
Conditions | Yield |
---|---|
addn. of tributyltin alkoxide to aldehyde; | 100% |
addn. of tributyltin alkoxide to aldehyde; | 100% |
tributyltin methoxide
1--1-methoxy-ethan
Conditions | Yield |
---|---|
With acetaldehyde In neat (no solvent) addn. of tributyltin alkoxides to aldehyde (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
With CH3CHO In neat (no solvent) addn. of tributyltin alkoxides to aldehyde (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
HOC(CH3)(C2H5)CH(CH3)COOCH3
tributyltin methoxide
(C4H9)3SnOC(CH3)(C2H5)CH(CH3)COOCH3
Conditions | Yield |
---|---|
byproducts: CH3OH; heating of equimolar amts. of educts, removing of alc.; | 100% |
byproducts: CH3OH; heating of equimolar amts. of educts, removing of alc.; | 100% |
2-(1-hydroxy-cyclopentyl)-propionic acid methyl ester
tributyltin methoxide
(C4H9)3SnOC5H8CH(CH3)COOCH3
Conditions | Yield |
---|---|
byproducts: CH3OH; equimolar amts. of educts, heating; remove alc.; | 100% |
byproducts: CH3OH; equimolar amts. of educts, heating; remove alc.; | 100% |
tributyltin methoxide
methyl 3-ethyl-3-hydroxy-2-methyl-pentanoate
(C4H9)3SnOC(C2H5)2CH(CH3)COOCH3
Conditions | Yield |
---|---|
byproducts: CH3OH; heating of equimolar amts. of educts, removing of alc.; | 100% |
byproducts: CH3OH; heating of equimolar amts. of educts, removing of alc.; | 100% |
HOC(CH3)(C3H7)CH(CH3)COOCH3
tributyltin methoxide
(C4H9)3SnOC(CH3)(C3H7)CH(CH3)COOCH3
Conditions | Yield |
---|---|
byproducts: CH3OH; heating of equimolar amts. of educts, removing of alc.; | 100% |
byproducts: CH3OH; heating of equimolar amts. of educts, removing of alc.; | 100% |
3-hydroxy-2-methyl-3-phenylbutyric acid methyl ester
tributyltin methoxide
(C4H9)3SnOC(CH3)(C6H5)CH(CH3)COOCH3
Conditions | Yield |
---|---|
byproducts: CH3OH; equimolar amts. of educts, heating; remove alc.; | 100% |
byproducts: CH3OH; equimolar amts. of educts, heating; remove alc.; | 100% |
methyl 3,3-diphenyl-3-hydroxy-2-methyl-propanoate
tributyltin methoxide
(C4H9)3SnOC(C6H5)2CH(CH3)COOCH3
Conditions | Yield |
---|---|
byproducts: CH3OH; equimolar amts. of educts, heating; remove alc.; | 100% |
byproducts: CH3OH; equimolar amts. of educts, heating; remove alc.; | 100% |
(R,S)-3-hydroxy-2,3-dimethylbutansaeuremethylester
tributyltin methoxide
(C4H9)3SnOC(CH3)2CH(CH3)COOCH3
Conditions | Yield |
---|---|
byproducts: CH3OH; heating of equimolar amts. of educts, removing of alc.; | 100% |
byproducts: CH3OH; heating of equimolar amts. of educts, removing of alc.; | 100% |
triethanolamine
tributyltin methoxide
tris(2-tri-n-butylstannoxyethyl)amine
Conditions | Yield |
---|---|
In benzene reflux (4 h); removal of solvent and excess educt by distn. in vacuo; elem. anal.; | 100% |
Conditions | Yield |
---|---|
In toluene byproducts: MeOH; under Ar, 3 equiv. of Sn-compd. and Te(OH)6 were heated in toluene at 85°C until Te-compd. was dissolved (ca. 4 h), then further 2 h at 110 °C; volatiles were removed in vac., elem. anal.; | 100% |
Trimethyl(methylthio)silane
tributyltin methoxide
tributyl(methylthio)stannane
Conditions | Yield |
---|---|
byproducts: (CH3)3SiOCH3; cooling, then heating; | 99% |
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: MeOH; mixt. of (-)-menthol and tributylmethoxystannane heated (formed MeOH removed continuously during react.); distn.; elem. anal.; | 99% |
1,1,1-tri(hydroxymethyl)propane
tributyltin methoxide
1,1,1-tris(tributyltinoxymethyl) propane
Conditions | Yield |
---|---|
In neat (no solvent) 1,1,1-trymethylolpropane to methoxytributyltin ratio 1:3; mixed, heatedat 100-150°C for 1 h at P=50 mm; evacuated to P=1 mm for 0.5 h, heated at 190-220°C; distd., IR, elem. anal.; | 99% |
Conditions | Yield |
---|---|
With (R)-(5-(tert-butylsulfinyl)spiro[benzo[d][1,3]dioxole-2,1'-cyclopentane]-4-yl)diphenylphosphine; copper(l) chloride In tetrahydrofuran at 20℃; for 12h; Glovebox; Inert atmosphere; enantioselective reaction; | 99% |
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