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(CH3)3SnCH2C6H4-m-Cl
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water byproducts: m-chlorotoluene; refluxing for 52 h;; | 85% |
With NaOH In ethanol; water byproducts: m-chlorotoluene; refluxing for 52 h;; | 85% |
In methanol; deuteromethanol byproducts: m-chlorotoluene; alkaline decompn. at 50°C;; | |
In methanol; deuteromethanol byproducts: m-chlorotoluene; alkaline decompn. at 50°C;; |
bis(trimethyltin)oxide
acetylene
A
trimethylstannylacetylene
B
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
at 8-12 atm in a sealed tube;; | A 65.5% B n/a |
2,6-dichloro-1,4-benzoquinone
hexamethyldistannane
A
C6Cl2H2(OSn(CH3)3)2
B
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
In benzene keeping at room temp. (N2) for 4 d; various yields in various conditions; evapn.; elem. anal.; | A 63% B n/a |
tris(trimethylstannyl)stibine
A
bis(trimethyltin)oxide
B
tetrakis(trimethylstannyl)distibane
C
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With oxygen In neat (no solvent) stibane left in air for 3 d; suspending in Ar-satd. acetone, decanting, recrystn. of red residue from toluene (2nd and 3rd product isolated from acetone suspn.); elem. anal.; | A n/a B 47% C n/a |
trimethyl(trimethylstannyl)silane
A
Hexamethyldisiloxane
B
hexamethyldistannane
C
trimethylstannane
D
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With bromobenzene; calcium In water for 1h; Ambient temperature; Further byproducts given; | A 36% B 8% C 42% D 10% |
trimethyl(trimethylstannyl)silane
A
Hexamethyldisiloxane
B
trimethyl(phenyl)stannane
C
hexamethyldistannane
D
trimethylstannane
E
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With bromobenzene; water; calcium In gas Ca vaporized at 900°C in vac. (ca. 5E-3 Torr), Me3SiSnMe3 introduced as vapor, mixed vapor condensed on cold (77 K) walls, warmed to room temp., excess of C6H5Br admitted as vapor, left to stand for 1 h, hydrolyzed with water; org. layer extd. with ether, products identified by GC-MASS, GLC; | A 36% B 2% C 8% D 42% E 10% |
trimethyltin bromide
A
tin
B
tetramethylstannane
C
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With zinc In water | |
With Zn In water |
Conditions | Yield |
---|---|
With F(1-) or Cl(1-) or CN(1-) In water byproducts: C6F5H; | |
With F(1-) or Cl(1-) or CN(1-) In ethanol; water byproducts: C6F5H; | |
With NaF or NaOH In water byproducts: C6HF5; |
2-(trimethylstannyl)-1-methylimidazole
A
1-methyl-1H-imidazole
B
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With water |
((methyl)3tin)2C(CON(methyl)2)2
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With water byproducts: N,N,N',N'-tetramethylmalondiamide; hydrolysis; |
trimethyl(trimethylstannyl)silane
A
Hexamethyldisiloxane
B
hexamethyldistannane
C
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With bromobenzene; water In gas Me3SiSnMe3 vapor condensed on cold (77 K) walls, warmed to room temp., excess of C6H5Br admitted as vapor, left to stand for 1 h, hydrolyzed with water; org. layer extd. with ether, products identified by GC-MASS, GLC; |
trichloromethyl-trimethyl tin
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With water In water byproducts: CHCl3; | |
With H2O In water byproducts: CHCl3; |
Conditions | Yield |
---|---|
In dimethyl sulfoxide byproducts: toluene; alkaline decompn.; mechanism discussed;; | |
In methanol byproducts: toluene; alkaline decompn.; mechanism discussed;; | |
In methanol; deuteromethanol Kinetics; byproducts: toluene; at 50°C; mechanism discussed;; |
Conditions | Yield |
---|---|
With water In methanol; water Kinetics; byproducts: C10H8; Irradiation (UV/VIS); decompn. in 95% aq. methanol on influence of light; mechanism discussed;; | |
In methanol byproducts: C10H8; alkaline decompn. in methanol;; | |
In methanol byproducts: C10H8; alkaline decompn. in methanol;; | |
With H2O In methanol; water Kinetics; byproducts: C10H8; Irradiation (UV/VIS); decompn. in 95% aq. methanol on influence of light; mechanism discussed;; |
methanol
1-(trimethylstannyl)-1,12-dicarba-closo-dodecaborane
A
1,12-dicarbora-closo-dodecaborane
B
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
In methanol Kinetics; hydrolysis;; | |
In methanol |
methanol
(CH3)3Sn-1,7-B10C2H11
A
1,7-dicarba-closo-dodecaborane(12)
B
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
In methanol Kinetics; hydrolysis;; | |
In methanol |
methanol
(CH3)3Sn-1,2-B10C2H11
A
1,2-dicarba-closo-dodecaborane(12)
B
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
In methanol Kinetics; hydrolysis;; | |
In methanol |
propan-1-ol
dichloromethyl-trimethyl tin
A
trimethyl-propoxytin
B
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With ammonia; water; ammonium chloride Kinetics; byproducts: CH2Cl2; Sn compd. placed into n-propanol-water in the presence of ammonia buffer (NH3/NH4Cl) at 25°C; products not isolated, determined by GLC; |
propan-1-ol
trimethyl(dibromomethyl)stanne
A
trimethyl-propoxytin
B
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With ammonia; water; ammonium chloride Kinetics; byproducts: CH2Br2; Sn compd. placed into n-propanol-water in the presence of ammonia buffer (NH3/NH4Cl) at 25°C; products not isolated, determined by GLC; |
2-trimethylstannylpyridine
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With water In water byproducts: C5H5N; | |
With H2O In water byproducts: C5H5N; |
1-trimethylstannyl-2-trifluoromethyl-3,3-difluoro-1-cyclopropene
A
2,2-difluoro-trifluoromethyl-cyclopropene
B
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
20 °C, hydrolysis;; | |
20 °C, hydrolysis;; |
1-(trimethylstannyl)-1,12-dicarba-closo-dodecaborane
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With potassium hydroxide In methanol Kinetics; byproducts: 1,12-B10C2H12; | |
With KOH In methanol Kinetics; byproducts: 1,12-B10C2H12; |
(CH3)3Sn-1,7-B10C2H11
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With potassium hydroxide In methanol Kinetics; byproducts: 1,7-B10C2H12; | |
With KOH In methanol Kinetics; byproducts: 1,7-B10C2H12; |
(CH3)3Sn-1,2-B10C2H11
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With potassium hydroxide In methanol Kinetics; byproducts: 1,2-B10C2H12; | |
With KOH In methanol Kinetics; byproducts: 1,2-B10C2H12; |
Trimethyl-(brom-dichlor-methyl)-stannan
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With water In water byproducts: CHBrCl2; hydrolysis;; | |
With H2O In water byproducts: CHBrCl2; hydrolysis;; |
Trimethyl-tribrom-methylstannan
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With water In water byproducts: CHBr3; hydrolysis;; | |
With H2O In water byproducts: CHBr3; hydrolysis;; |
Conditions | Yield |
---|---|
With H2O In water byproducts: CH3CON(CH3)2; |
Trimethyl--stannan
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With H2O byproducts: CH2CHCCH; |
(CH3)3SnCH2C6H4-p-Br
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
With sodium hydroxide In methanol Kinetics; byproducts: p-bromotoluene; | |
With NaOH In methanol Kinetics; byproducts: p-bromotoluene; |
N-{(triethylstannyloxysulphonyl)maleoyl}amino acetic acid
trimethyltin(IV) hydroxide
trimethyltin N-{(triethylstannyloxysulphonyl)maleoyl}amino acetate
Conditions | Yield |
---|---|
In ethanol addn. of Me3SnOH to a soln. of the other Sn compound in ethyl alcohol; heated for 3 h at 90°C;; removal of solvent by distn.; kept in vac. at 90°C for 2-3 h; elem. anal.;; | 99% |
Conditions | Yield |
---|---|
In methanol soln. AcMet in methanol added to soln. SnMe3(OH) in methanol and stirred overnight or refluxed for 2 h; solvent evapd., diethyl ether and light petroleum (b.p. 40-60°C)added and mixt. kept in freezer, crystals washed and dried in vacuo; elem. anal.; | 99% |
Conditions | Yield |
---|---|
In toluene at -78 - 20℃; Schlenk technique; | 99% |
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 70℃; for 24h; | 98% |
Conditions | Yield |
---|---|
In benzene byproducts: H2O; mixing tin-compd. and oxime in anhyd. benzene under exclusion of moisture, refluxing; removal of water azeotropically (azeotropic dehydration technique on the Dean-Stark assembly), removal of excess benzene by distn. under reduced pressure, elem. anal.; | 97% |
N-{(tributylstannyloxysulphonyl)maleoyl}amino acetic acid
trimethyltin(IV) hydroxide
trimethyltin N-{(tributylstannyloxysulphonyl)maleoyl}amino acetate
Conditions | Yield |
---|---|
In ethanol addn. of Me3SnOH to a soln. of the other Sn compound in ethyl alcohol; heated for 3 h at 90°C;; removal of solvent by distn.; kept in vac. at 90°C for 2-3 h; elem. anal.;; | 96% |
Conditions | Yield |
---|---|
In benzene Sn compd. and org. compd. (molar ratio 1:1) refluxed in benzene for 4 htill no more water distilled out azeotropically; distn., addn. of hexane, drying in vac. at 28°C and 0.1 mm for 2h; elem. anal.; | 96% |
N-(3-methylphenyl)-benzylamine oxime
trimethyltin(IV) hydroxide
Conditions | Yield |
---|---|
In benzene Sn compd. and org. compd. (molar ratio 1:1) refluxed in benzene for 5 htill no more water distilled out azeotropically; distn., addn. of hexane, drying in vac. at 28°C and 0.1 mm for 2h; elem. anal.; | 95% |
trimethyltin(IV) hydroxide
2-benzylideneamino-benzoic acid
(N-benzalanthranilato)trimethyltin(IV)
Conditions | Yield |
---|---|
In benzene byproducts: H2O; react. under anhydrous conditions, addn. of Me3SnOH to N-benzalanthranilic acid in benzene, refluxing; removal of liberated water azeotropically with benzene at 69°C, elem. anal.; | 94% |
Conditions | Yield |
---|---|
In chloroform byproducts: H2O; treatment of Me3SnOH with equimolar amt. of thiol until dissoln. (roomtemp.); drying (Na2SO4), partial evapn. (reduced pressure, 10°C), addn. of petroleum ether, cooling (refrigerator, overnight), washing (petroleum ether/Et2O=1:1), drying (vac., 10°C); elem. anal.; | 94% |
2,3-dibromomaleimide
trimethyltin(IV) hydroxide
2,3-dibromo-N-(trimethylstannyl)maleimide
Conditions | Yield |
---|---|
In not given byproducts: H2O; solvent toluene or heptane; azeotropic removal water and solvent, recrystn.; elem. anal.; | 94% |
Conditions | Yield |
---|---|
In toluene byproducts: water; N2-atmosphere; stoich. amts., refluxing for 20 h (distn. off of water); evapn. (reduced pressure), dissoln. in Et2O, filtration, evapn. (vac.); elem. anal.; | 94% |
N-{(4-triethylstannyloxysulphonyl)phthaloyl}amino acetic acid
trimethyltin(IV) hydroxide
trimethyltin N-{(4-triethylstannyloxysulphonyl)phthaloyl}amino acetate
Conditions | Yield |
---|---|
In ethanol addn. of Me3SnOH to a soln. of the other Sn compound in ethyl alcohol; heated for 3 h at 90°C;; removal of solvent by distn.; kept in vac. at 90°C for 2-3 h; elem. anal.;; | 92% |
dithio terephthalic acid
trimethyltin(IV) hydroxide
(CH3)3SnSOCC6H4COSSn(CH3)3
Conditions | Yield |
---|---|
In methanol (N2); soln. of metal compd. in dry MeOH was added to MeOH soln. of acid (2:1 mol) over a period of 15 min.; after stirring for 1 h mixt. was dried in vac.; residue suspd. in warm MeOH, filtered and dried in vac. over silicagel; stored at 0°C in total darkness; elem. anal.; | 91% |
N-{(4-tributylstannyloxysulphonyl)phthaloyl}amino acetic acid
trimethyltin(IV) hydroxide
trimethyltin N-{(4-tributylstannyloxysulphonyl)phthaloyl}amino acetate
Conditions | Yield |
---|---|
In ethanol addn. of Me3SnOH to a soln. of the other Sn-compound in ethyl alcohol; heated for 3 h at 90°C;; removal of solvent by distn.; kept in vac. at 90°C for 2-3 h; elem. anal.;; | 91% |
Conditions | Yield |
---|---|
In benzene byproducts: H2O; mixing tin-compd. and oxime together in benzene under exclusion of moisture, refluxing; removal of water azeotropically (azeotropic dehydration technique on the Dean-Stark assembly), removal of excess solvent by distn. under reduced pressure, elem. anal.; | 91% |
Conditions | Yield |
---|---|
In benzene byproducts: H2O; addn. of o-anisic acid to a suspension of the Sn-compd. in benzene, heating under reflux for 4 h with a Dean-Stark separator; removing of solvent, recrystn. from CH2Cl2/Skelly mixt.; elem. anal.; | 90.2% |
tributylstannyloxysulphonylmaleic anhydride
trimethyltin(IV) hydroxide
bis-trimethyltin(tributylstannyloxysulphonyl)maleate
Conditions | Yield |
---|---|
In acetonitrile dropwise addn. of a soln. of trimethyltin hydroxide to a soln. of the other Sn compound in acetonitrile; stirring for 2-3 h at 90°C;; removal of solvent to dryness; purified in boiling alcohol with activated carbon; pptn.; elem. anal.;; | 90% |
Conditions | Yield |
---|---|
In chloroform slow heating of Sn-compd. and diketone in chloroform under reflux for 4-8 h, continuous fractionating out formed water during this period; removal of solvent at 35-40°C/2 mm, elem. anal.; | 90% |
In benzene slow heating of Sn-compd. and diketone in benzene under reflux for 4-8 h, continuous fractionating out formed water during this period; removal of solvent at 35-40°C/2 mm, elem. anal.; | 90% |
N-phthaloylglycine
trimethyltin(IV) hydroxide
C6H4(CO)2NCH2COOSn(CH3)3
Conditions | Yield |
---|---|
In toluene byproducts: H2O; refluxed 15 min; toluene-water azeotrope fractionated out, solvent distd. off, residue evapd. in vacuo to dryness, recrystd. from toluene, elem. anal.; | 90% |
2-(2,5-dioxopyrrolidin-1-yl)acetic acid
trimethyltin(IV) hydroxide
(CH2)2(CO)2NCH2COOSn(CH3)3
Conditions | Yield |
---|---|
In toluene byproducts: H2O; refluxed 15 min; toluene-water azeotrope fractionated out, solvent distd. off, residue evapd. in vacuo to dryness, recrystd. from toluene/heptane, elem. anal.; | 90% |
2-methyl-2-phthalimidopropanoic acid
trimethyltin(IV) hydroxide
C6H4(CO)2NC(CH3)2COOSn(CH3)3
Conditions | Yield |
---|---|
In toluene byproducts: H2O; refluxed 15 min; toluene-water azeotrope fractionated out, solvent distd. off, residue evapd. in vacuo to dryness, recrystd. from toluene/heptane, elem. anal.; | 90% |
1-(3-aminophenyl)ethanone oxime
trimethyltin(IV) hydroxide
(CH3)3SnONC(CH3)C6H4NH2
Conditions | Yield |
---|---|
In benzene byproducts: H2O; mixing tin-compd. and oxime together in benzene under exclusion of moisture, refluxing; removal of water azeotropically (azeotropic dehydration technique on the Dean-Stark assembly), removal of excess solvent by distn. under reduced pressure, elem. anal.; | 90% |
p-aminoacetophenone oxime
trimethyltin(IV) hydroxide
(CH3)3SnONC(CH3)C6H4NH2
Conditions | Yield |
---|---|
In benzene byproducts: H2O; mixing tin-compd. and oxime in anhyd. benzene under exclusion of moisture, refluxing; removal of water azeotropically (azeotropic dehydration technique on the Dean-Stark assembly), removal of excess benzene by distn. under reduced pressure, elem. anal.; | 90% |
Conditions | Yield |
---|---|
In toluene 4-ketopimelic acid and Me3SnOH were refluxed in toluene for 2 h at 125°C; filtered; elem. anal.; | 90% |
trimethylstannyloxysulphonylmaleic anhydride
trimethyltin(IV) hydroxide
bis-trimethyltin(trimethylstannyloxysulphonyl)maleate
Conditions | Yield |
---|---|
In acetonitrile dropwise addn. of a soln. of trimethyltin hydroxide to a soln. of the other Sn compound in acetonitrile; stirring for 2-3 h at 90°C;; removal of solvent to dryness; purified in boiling alcohol with activated carbon; pptn.; elem. anal.;; | 88% |
triethylstannyloxysulphonylmaleic anhydride
trimethyltin(IV) hydroxide
bis-trimethyltin(triethylstannyloxysulphonyl)maleate
Conditions | Yield |
---|---|
In acetonitrile dropwise addn. of a soln. of trimethyltin hydroxide to a soln. of the other Sn compound in acetonitrile; stirring for 2-3 h at 90°C;; removal of solvent to dryness; purified in boiling alcohol with activated carbon; pptn.; elem. anal.;; | 88% |
trimethyltin(IV) hydroxide
2,2'-bis-(1,2-dihydro-4-oxo-3,1-benzoxazine)
Conditions | Yield |
---|---|
In benzene byproducts: H2O; in refluxing benzene; H2O was removed as azeotrope of benzene; elem. anal.; | 88% |
rac-3-sulfanylpropane-1,2-diol
trimethyltin(IV) hydroxide
(CH3)3SnSCH2CHOHCH2OH
Conditions | Yield |
---|---|
In chloroform byproducts: H2O; treatment of Me3SnOH with equimolar amt. of thiol until dissoln. (roomtemp.); drying (Na2SO4), partial evapn. (reduced pressure, 10°C), addn. of petroleum ether, cooling (refrigerator, overnight), washing (petroleum ether/Et2O=1:1), drying (vac., 10°C); elem. anal.; | 88% |
4-chloro-1,3-benzenedithiol
trimethyltin(IV) hydroxide
((CH3)3Sn)2C6H3ClS2
Conditions | Yield |
---|---|
In methanol addn. of soln. of dithiol in methanol to a suspension of corresponding tin(IV) compd. in methanol; 2h, pptn.;; recrystn. ppt. from CHCl3; elem. anal.;; | 87% |