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594-27-4

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594-27-4 Usage

Chemical Properties

clear colorless liquid

Uses

Different sources of media describe the Uses of 594-27-4 differently. You can refer to the following data:
1. Tetramethyltin is used in many organic syntheticreactions.
2. Tetramethylstannane is used in preparation of Biphenyl Pyrazines as PD-1/PD-L1 inhibitors for treating cancer.

Definition

ChEBI: An organotin compound carrying four methyl groups.

Health Hazard

Tetramethyltin is moderately toxic by allroutes of exposure. The symptoms includeheadache, muscle weakness, and paralysis.Exposure limits:TLV-TWA: 0.1 mg (Sn)/m3 (skin) (ACGIH)PEL-TWA: 0.1 mg (Sn)/m3 (skin) (OSHA).

Fire Hazard

The ease of oxidation, however, is low in comparison with most other metal alkyls. It is relatively stable to air and does not ignite spontaneously as other alkyls do. Also, it is stable in water. The compound, however, is highly flammable, the flash point being ( -13°C) 9°F (Aldrich 1996). It explodes violently in contact with dinitrogen tetraoxide even, at -80°C (-112°F) (Bailar 1973). Reaction with strong oxidizers is expected to be vigorous to violent.

Safety Profile

Moderately toxic by inhalation. A very dangerous fire and explosion hazard when exposed to heat, flame, or oxidizers. Powerful explosive reaction with dinitrogen tetroxide. To fight fire, use water, foam, CO2, dry chemical. When heated it emits acrid smoke and irritating fumes. See also TIN COMPOUNDS and ORGANOMETALS.

Purification Methods

It is purified by fractionation using a Todd column (p 11) of 35-40 plates at atmospheric pressure. The purity of the fractions can be followed by IR [Edgell & Ward J Am Chem Soc 77 6486 1955]. It readily dissolves stopcock silicone greases which give bands in the 8-10a region. [Edgell & Ward J Am Chem Soc 76 1169 1954, Beilstein 4 IV 4307.]

Check Digit Verification of cas no

The CAS Registry Mumber 594-27-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 4 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 594-27:
(5*5)+(4*9)+(3*4)+(2*2)+(1*7)=84
84 % 10 = 4
So 594-27-4 is a valid CAS Registry Number.
InChI:InChI=1/4CH3.Sn/h4*1H3;/rC4H12Sn/c1-5(2,3)4/h1-4H3

594-27-4 Well-known Company Product Price

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  • TCI America

  • (T0919)  Tetramethyltin  >97.0%(GC)

  • 594-27-4

  • 5g

  • 370.00CNY

  • Detail
  • TCI America

  • (T0919)  Tetramethyltin  >97.0%(GC)

  • 594-27-4

  • 25g

  • 995.00CNY

  • Detail
  • Alfa Aesar

  • (71145)  Tetramethyltin, 98%   

  • 594-27-4

  • 2g

  • 230.0CNY

  • Detail
  • Alfa Aesar

  • (71145)  Tetramethyltin, 98%   

  • 594-27-4

  • 10g

  • 760.0CNY

  • Detail
  • Alfa Aesar

  • (71145)  Tetramethyltin, 98%   

  • 594-27-4

  • 50g

  • 3039.0CNY

  • Detail

594-27-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name tetramethyltin

1.2 Other means of identification

Product number -
Other names Stannane, tetramethyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:594-27-4 SDS

594-27-4Synthetic route

methyl bromide
74-83-9

methyl bromide

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
With {(C2H5)4N}Br In acetonitrile Electrolysis; Sn-cathode, 50°C;100%
With {(C2H5)4N}Br In acetonitrile Electrolysis; Sn-cathode, 50°C;100%
In water; acetonitrile Electrolysis; Sn-cathode, Pt-anode, 0.25 M Et4NClO4 in MeCN/water=7:1, 25°C, 10mA/cm**(-2); gas chromy.;
tin(IV) chloride
7646-78-8

tin(IV) chloride

Dimethylaluminium-acetylacetonat

Dimethylaluminium-acetylacetonat

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In benzene molar ratio 2 : 1, room temp.;100%
In benzene molar ratio 2 : 1, room temp.;100%
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

sodium methylate
124-41-4

sodium methylate

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
80°C;99%
80°C;99%
cis-methyl 2-trimethylstannyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate

cis-methyl 2-trimethylstannyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

cis-methyl 2-chlorodimethylstannyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate

cis-methyl 2-chlorodimethylstannyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In neat (no solvent) stirring under N2, helding at room temp. for 4 h; destilling Me3SnCl and Me4Sn off under reduced pressure, recrystn. from ethanol, elem. anal.;A 96%
B n/a
methylene chloride
74-87-3

methylene chloride

tin(IV) chloride
7646-78-8

tin(IV) chloride

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In further solvent(s) equimolar NaCl-AlCl3 melt, 220°C;95%
In further solvent(s) equimolar NaCl-AlCl3 melt, 220°C;95%
(C6H3(CH2NMe2)2-2,6)SnMe3

(C6H3(CH2NMe2)2-2,6)SnMe3

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

A

[(C6H3(CH2NMe2)2-2,6)SnMe2](Me3SnCl2)

[(C6H3(CH2NMe2)2-2,6)SnMe2](Me3SnCl2)

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In dichloromethane N2-atmosphere; refluxing for 72 h; evapn., addn. of hexane, collection (filtration), drying (vac.); elem. anal.;A 95%
B n/a
cis-methyl 2-trimethylstannylcyclohexanecarboxylate

cis-methyl 2-trimethylstannylcyclohexanecarboxylate

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

cis-methyl 2-chlorodimethylstannylcyclohexanecarboxylate

cis-methyl 2-chlorodimethylstannylcyclohexanecarboxylate

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In neat (no solvent) stirring under N2, room temp., 6 h.; Evapn., recrystn. (ethanol). Elem. anal.;A 93.5%
B n/a
Sn(4+)*3C6H5CH2(1-)*Cl(1-)=(C6H5CH2)3SnCl

Sn(4+)*3C6H5CH2(1-)*Cl(1-)=(C6H5CH2)3SnCl

methyllithium
917-54-4

methyllithium

A

tetramethylstannane
594-27-4

tetramethylstannane

B

benzyllithium
766-04-1

benzyllithium

C

lithium chloride

lithium chloride

Conditions
ConditionsYield
In diethyl etherA 92%
B n/a
C n/a
In diethyl etherA 92%
B n/a
C n/a
1,3-dimethyl-2-(trimethylstannyl)-2-bora-1,3-diazacyclopentane
36333-59-2

1,3-dimethyl-2-(trimethylstannyl)-2-bora-1,3-diazacyclopentane

dimethyl(1,2-bis(dimethylphosphino)ethane)palladium(II)
15630-15-6

dimethyl(1,2-bis(dimethylphosphino)ethane)palladium(II)

A

1,2,3-trimethyl-[1,3,2]diazaborolidine
29173-12-4

1,2,3-trimethyl-[1,3,2]diazaborolidine

(((CH3)2PCH2)2)Pd(Sn(CH3)3)(BN2C2H4(CH3)2)

(((CH3)2PCH2)2)Pd(Sn(CH3)3)(BN2C2H4(CH3)2)

C

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In benzene-d6 130°C (17 h); recrystn. (toluene / pentane = 1 : 4); elem. anal.;A 91%
B 68%
C 84%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

tin(IV) chloride
7646-78-8

tin(IV) chloride

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In dibutyl ether90%
In dibutyl ether90%
In dibutyl ether89%
Tetramethylblei-(IV)
75-74-1

Tetramethylblei-(IV)

tin(IV) chloride
7646-78-8

tin(IV) chloride

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In toluene boiling;90%
In toluene boiling;90%
hexamethyldistannane
661-69-8

hexamethyldistannane

lithium tetramethyl alanate
14281-94-8, 32661-49-7, 32661-50-0

lithium tetramethyl alanate

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
20 h heating at 80°C;90%
20 h heating at 80°C;90%
Me3Sn(N(isobutyl)2)
174837-79-7

Me3Sn(N(isobutyl)2)

trimethyl gallium
1445-79-0

trimethyl gallium

A

[Me2Ga(N(isobutyl)2)]2

[Me2Ga(N(isobutyl)2)]2

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In neat (no solvent) N2 or Ar-atmosphere; heating soln. of Me3Ga and Sn-compound at 55-56°C for 6 h; evapn., recrystn. (pentane); elem. anal.;A 88.6%
B n/a
(CH3)2Sn(CH2CH2CH2)2O
110971-32-9

(CH3)2Sn(CH2CH2CH2)2O

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

A

5-chloro-5-methyl-1-oxa-5-stannabicylco{3.3.0(1,5)}octane
110971-31-8

5-chloro-5-methyl-1-oxa-5-stannabicylco{3.3.0(1,5)}octane

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In neat (no solvent) Under Ar, heating of Me2Sn(CH2CH2CH2)2NMe and Me3SnCl (1h, 120°C).; Me4Sn is removed, recrystn. from CH2Cl2/hexane, elem. anal..;A 87%
B n/a
1,1'-bis(trichlorostannyl)ferrocene
220231-14-1

1,1'-bis(trichlorostannyl)ferrocene

trimethyl gallium
1445-79-0

trimethyl gallium

A

1,1'-bis(dimethylgallyl)ferrocene

1,1'-bis(dimethylgallyl)ferrocene

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In toluene under Ar atm. Me3Ga was added to suspn. 1,1'-bis(trichlorostannyl)ferrocene in toluene and heated to 68°C; react. mixt. was cooled to room temp., supernatant soln. was decanted, residue was washed with hexane (or toluene) and driedin vac.; elem. anal.;A 86%
B n/a
methyl magnesium iodide
917-64-6

methyl magnesium iodide

tin(IV) chloride
7646-78-8

tin(IV) chloride

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In diethyl ether equivalent amts. of educts, cooling with ice, dropping SnCl4, 5 to 6 h heating; distn.;85%
In diethyl ether equivalent amts. of educts, cooling with ice, dropping SnCl4, 5 to 6 h heating; distn.;85%
In diethyl ether equivalent amts. of educts, cooling with ice, dropping SnCl4, 5 to 6 h heating; distn.;45%
trimethyltin fluoride
420-60-0

trimethyltin fluoride

pentamethylantimony
15120-50-0

pentamethylantimony

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
85%
85%
(dibutylamino)trimethylstannane
1068-79-7

(dibutylamino)trimethylstannane

tri-tert-butylindium(III)
113088-72-5

tri-tert-butylindium(III)

A

In(C(CH3)3)3*HN((CH2)3CH3)2

In(C(CH3)3)3*HN((CH2)3CH3)2

B

(di-n-butylamino)di-tertbutylindane

(di-n-butylamino)di-tertbutylindane

C

hexamethyldistannane
661-69-8

hexamethyldistannane

D

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In neat (no solvent) byproducts: HNBu2, isobutane, isobutene; Irradiation (UV/VIS); inert atmosphere; equimolar amts., room light, 25°C, 3 weeks (crystn.); recrystn. (CH2Cl2); elem. anal.; further unidentified products;A n/a
B 82%
C n/a
D n/a
Tetrakis--silan
18365-38-3

Tetrakis--silan

A

(C4H8O)3LiSi(Sn(CH3)3)3

(C4H8O)3LiSi(Sn(CH3)3)3

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran; diethyl ether under N2 or Ar, dropwise addn. of MeLi in THF/Et2O to Si(SnMe3)4 in THF , stirred for 22 h; removal of volatiles, extn. (pentane), concd., cooled to -40°C, filtered, dried (four crops);A 81.2%
B n/a
tin(IV) chloride
7646-78-8

tin(IV) chloride

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
With methyl magnesium iodide In dibutyl ether (N2);81%
Me3Sn(N(cyclohexyl)2)
1084-14-6

Me3Sn(N(cyclohexyl)2)

trimethyl gallium
1445-79-0

trimethyl gallium

A

[Me2Ga(N(cyclohexyl)2)]2

[Me2Ga(N(cyclohexyl)2)]2

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In neat (no solvent) N2 or Ar-atmosphere; standing soln. of Me3Ga and Sn-compound at room temp. for 20.3 h; evapn., recrystn. (pentane); elem. anal.;A 81%
B n/a
Me3Sn(tropolonate)

Me3Sn(tropolonate)

A

[Sn(CH3)2(C7H5O2)2]

[Sn(CH3)2(C7H5O2)2]

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In solid Sn-complex was heated to 60°C for 0.5 h; recrystd. from hot Et2O, dried;A 80%
B n/a
In solid Irradiation (UV/VIS); Sn-complex was exposed to daylight simulation radiation (>360 nm) for 24 h; recrystd. from hot Et2O, dried; elem. anal.;A 70.5%
B n/a
methylmagnesium chloride
676-58-4

methylmagnesium chloride

tin(IV) chloride
7646-78-8

tin(IV) chloride

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In tetrahydrofuran treating with satd. aq. citric acid soln.;78%
In 1,2-dimethoxyethane treating with satd. aq. citric acid soln.;78%
In tetrahydrofuran treating with satd. aq. citric acid soln.;78%
Diethylamino-trimethyl-stannan
1068-74-2

Diethylamino-trimethyl-stannan

tri-tert-butylindium(III)
113088-72-5

tri-tert-butylindium(III)

A

In(C(CH3)3)3*HN(C2H5)2

In(C(CH3)3)3*HN(C2H5)2

B

(diethylamino)di-tertbutylindane

(diethylamino)di-tertbutylindane

C

hexamethyldistannane
661-69-8

hexamethyldistannane

D

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In neat (no solvent) byproducts: HNEt2, isobutane, isobutene; Irradiation (UV/VIS); inert atmosphere; equimolar amts., room light, 25°C, 2-3 weeks; recrystn. (CH2Cl2); elem. anal.; further unidentified products;A 12%
B 78%
C n/a
D n/a
2,5-bis(trimethylstannyl)-1,5-hexadiene
90886-28-5

2,5-bis(trimethylstannyl)-1,5-hexadiene

methyllithium
917-54-4

methyllithium

A

2-(trimethylstannyl)-1,5-hexadiene
125405-30-3

2-(trimethylstannyl)-1,5-hexadiene

B

bis(2-hexa-1,5-dienyl)dimethylstannane
134940-88-8

bis(2-hexa-1,5-dienyl)dimethylstannane

C

1-(2-hexa-1,5-dienyl)-1-methyl-2,5-bis(methylene)stannolane
134967-25-2

1-(2-hexa-1,5-dienyl)-1-methyl-2,5-bis(methylene)stannolane

D

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In tetrahydrofuran under argon, compounds were added at -78°C, stirring at this temp. for 5 min, mixt. was warmed to 25°C for 10 min and cooled to -78°C, mixt was transfered to a soln. of water in THF; solvent was removed under vacuum, resulting oil was purified by glpc, elem. anal., mass spectrum;A 11%
B 14%
C 75%
D n/a
Bis(trimethylstannyl)sulfur diimide
50518-65-5

Bis(trimethylstannyl)sulfur diimide

A

N-lithio-N'-trimethylstannylsulfurdiimide

N-lithio-N'-trimethylstannylsulfurdiimide

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
With methyllithium In not given equimolar amts. of MeLi and stannylsulfurdiimide reacting under Ar, Me4Sn removing by fractional distn.; identified by elem. anal., IR and NMR spectra;A 74.5%
B 41%
methyllithium
917-54-4

methyllithium

hexamethyldistannane
661-69-8

hexamethyldistannane

trimethylstannane
1631-73-8

trimethylstannane

A

hydrogen
1333-74-0

hydrogen

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In diethyl ether Sn2Me6 (1.12 mmol) in Et2O treated with MeLi (1.20 mmol, 1.00 M soln. in Et2O) under Ar, stirred for 30 min at 0°C, TMTH (1.12 mmol) added via syringe, stirred for 30 min at room temp., cooled to 0°C, quenched with water; H2 collected with gas measuring device, GC analysis of org. layer;A 74%
B n/a
trifluoroacetyl iodide
354-36-9

trifluoroacetyl iodide

hexamethyldistannane
661-69-8

hexamethyldistannane

A

tetramethylstannane
594-27-4

tetramethylstannane

B

trimethylstannyl iodide
811-73-4

trimethylstannyl iodide

C

trimethyl(trifluoromethyl)tin
754-25-6

trimethyl(trifluoromethyl)tin

Conditions
ConditionsYield
In not given byproducts: CO, CHF3, CF3I; for 4 h;;A n/a
B n/a
C 74%
In not given byproducts: CO, CHF3, CF3I; for 4 h;;A n/a
B n/a
C 74%
trimethyltin(IV) dimesylamide

trimethyltin(IV) dimesylamide

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

{(CH3)2Sn(CH3S(O)CH3)4}(2+)*2{N(SO2CH3)2}(1-)={(CH3)2Sn(CH3S(O)CH3)4}{N(SO2CH3)2}2

{(CH3)2Sn(CH3S(O)CH3)4}(2+)*2{N(SO2CH3)2}(1-)={(CH3)2Sn(CH3S(O)CH3)4}{N(SO2CH3)2}2

B

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
In tetrachloromethane dropwise addn. of dimethylsulfoxide (15.4mmol) to refluxing suspension of (CH3)3SnN(SO2CH3) in CCl4 (50ml), formation of a clear soln:; formation of crystals after 3d, -15°C; idenification of tetramethyl tin by GC-MS coupling;;A 74%
B n/a
1-methyl-2-trimethylstannyl pyrrole

1-methyl-2-trimethylstannyl pyrrole

benzaldehyde
100-52-7

benzaldehyde

tetramethylstannane
594-27-4

tetramethylstannane

Conditions
ConditionsYield
12h, 195°C;73%
12h, 195°C;73%
2-bromo-5-hydroxy-[1,4]naphthoquinone
69008-03-3

2-bromo-5-hydroxy-[1,4]naphthoquinone

tetramethylstannane
594-27-4

tetramethylstannane

5-hydroxy-2-methyl-1,4-naphthoquinone
481-42-5

5-hydroxy-2-methyl-1,4-naphthoquinone

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0); copper(I) bromide In 1,4-dioxane for 15h; Heating;100%
tetrakis(triphenylphosphine) palladium(0); copper(I) bromide In 1,4-dioxane for 15h; Heating; Yield given;
tetramethylstannane
594-27-4

tetramethylstannane

4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.166667h; Mechanism;100%
With bis(η3-allyl-μ-chloropalladium(II)) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.166667h;100%
With benzoylchlorobis(triphenylphosphine)palladium(II) In chloroform at 65℃; for 24h;95%
With N,N,N,N,N,N-hexamethylphosphoric triamide; poly-γ-(diphenylphosphino)propylsiloxane palladium(0) at 65℃; for 20h;83%
tetramethylstannane
594-27-4

tetramethylstannane

(2R,3S,4S)-4-[(tert-Butyldimethylsilyl)oxy]-2,3-epoxy-6-iodo-5-cyclohexen-1-one
188308-06-7

(2R,3S,4S)-4-[(tert-Butyldimethylsilyl)oxy]-2,3-epoxy-6-iodo-5-cyclohexen-1-one

(+)-(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-methyl-1-cyclohex-5-en-1-one
162809-82-7

(+)-(2R,3S,4S)-4-tert-butyldimethylsilyloxy-2,3-epoxy-6-methyl-1-cyclohex-5-en-1-one

Conditions
ConditionsYield
With copper(l) iodide; triphenyl-arsane; diethylamine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran at 80℃; for 24h; Stille reaction;100%
C24H24BrFN2O4
1007204-86-5

C24H24BrFN2O4

tetramethylstannane
594-27-4

tetramethylstannane

ethyl (3S)-(3-benzyloxycarbonylamino-6-fluoro-8-methyl-1,2,3,4-tetrahydro-9H-carbazol-9-yl)-acetate
1007202-02-9

ethyl (3S)-(3-benzyloxycarbonylamino-6-fluoro-8-methyl-1,2,3,4-tetrahydro-9H-carbazol-9-yl)-acetate

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃;100%
4-nitrobenzenediazonium o-benzenedisulfonimide

4-nitrobenzenediazonium o-benzenedisulfonimide

tetramethylstannane
594-27-4

tetramethylstannane

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

Conditions
ConditionsYield
palladium diacetate In tetrahydrofuran at 40℃; for 0.5h;100%
tetramethylstannane
594-27-4

tetramethylstannane

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
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%
N-Boc 10-bromocytisine

N-Boc 10-bromocytisine

tetramethylstannane
594-27-4

tetramethylstannane

N-Boc 10-methylcytisine

N-Boc 10-methylcytisine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride In toluene at 100℃; for 24h; Inert atmosphere;
Trichlorbutylstannan
1118-46-3

Trichlorbutylstannan

tetramethylstannane
594-27-4

tetramethylstannane

A

dimethyltin dichloride
753-73-1

dimethyltin dichloride

B

butyl-methyl-tin dichloride
15649-24-8

butyl-methyl-tin dichloride

Conditions
ConditionsYield
2-fold excess of C4H9SnCl3, 180°C, 2h;A n/a
B 99.4%
2-fold excess of C4H9SnCl3, 180°C, 2h;A n/a
B 99.4%
tetramethylstannane
594-27-4

tetramethylstannane

(Z)-methyl 4-(2-bromo-2-phenylvinyl)benzoate
253684-52-5

(Z)-methyl 4-(2-bromo-2-phenylvinyl)benzoate

methyl 4-[(E)-2-methyl-2-phenylvinyl]benzoate

methyl 4-[(E)-2-methyl-2-phenylvinyl]benzoate

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl-formamide at 80℃; for 10h; Stille reaction;99%
tetramethylstannane
594-27-4

tetramethylstannane

2-benzyl-10-methyl-1-oxo-1,2,3,10-tetrahydroazepino[3,4-b]indol-5-yl trifluoromethanesulfonate
292150-59-5

2-benzyl-10-methyl-1-oxo-1,2,3,10-tetrahydroazepino[3,4-b]indol-5-yl trifluoromethanesulfonate

2-benzyl-5,10-dimethyl-1,2,3,10-tetrahydroazepino[3,4-b]indol-1-one

2-benzyl-5,10-dimethyl-1,2,3,10-tetrahydroazepino[3,4-b]indol-1-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide at 100℃; for 2h; Stille reaction;99%
tetramethylstannane
594-27-4

tetramethylstannane

5-bromopyridin-3-yl 4-methylbenzenesulfonate
458569-33-0

5-bromopyridin-3-yl 4-methylbenzenesulfonate

5-methylpyridin-3-yl 4-methylbenzenesulfonate
458569-34-1

5-methylpyridin-3-yl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 17h;99%
tetramethylstannane
594-27-4

tetramethylstannane

(2S,3S,4aR,8aR)-2,3,4a,5,6,8a-hexahydro-7-iodo-2,3-dimethoxy-2,3-dimethylbenzo[b][1,4]dioxin-6-one
334700-48-0

(2S,3S,4aR,8aR)-2,3,4a,5,6,8a-hexahydro-7-iodo-2,3-dimethoxy-2,3-dimethylbenzo[b][1,4]dioxin-6-one

(2S,3S,4aR,8aR)-2,3-Dimethoxy-2,3,7-trimethyl-2,3,4a,8a-tetrahydro-5H-benzo[1,4]dioxin-6-one

(2S,3S,4aR,8aR)-2,3-Dimethoxy-2,3,7-trimethyl-2,3,4a,8a-tetrahydro-5H-benzo[1,4]dioxin-6-one

Conditions
ConditionsYield
With copper(l) iodide; triphenyl-arsane; diethylamine; tris(dibenzylideneacetone)dipalladium chloroform complex In tetrahydrofuran at 100℃; for 24h; Stille reaction;99%
tetramethylstannane
594-27-4

tetramethylstannane

tin(IV) chloride
7646-78-8

tin(IV) chloride

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

Conditions
ConditionsYield
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
594-27-4

tetramethylstannane

phenyltin trichloride
1124-19-2

phenyltin trichloride

A

trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

B

methylphenyltin(IV) dichloride
15649-26-0

methylphenyltin(IV) dichloride

Conditions
ConditionsYield
equimolar amts. of educts, 0°C, 1.5h;A 99%
B 85%
equimolar amts. of educts, 0°C, 1.5h;A 99%
B 85%
dodecatungstosilic acid

dodecatungstosilic acid

tetramethylstannane
594-27-4

tetramethylstannane

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

[α-SiW12O40][trimethyltin(DMSO)2]*2DMSO

[α-SiW12O40][trimethyltin(DMSO)2]*2DMSO

Conditions
ConditionsYield
In dimethyl sulfoxide byproducts: methane; under inert atmosphere; anhyd. H4SiW12O40 dissolved in anhyd. DMSO; freezed at 0°C; Me4Sn added; stirred at 50°C for 2 d; half of solvent and excess Me4Sn removed under vac. at 200°C; dissolved by heating at 50°C; kept at room temp. overnight;99%
5-bromoveratralaldehyde
6948-30-7

5-bromoveratralaldehyde

tetramethylstannane
594-27-4

tetramethylstannane

3,4-dimethoxy-5-methylbenzaldehyde
80547-80-4

3,4-dimethoxy-5-methylbenzaldehyde

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In N,N-dimethyl-formamide at 100℃; for 3h; Stille coupling; Inert atmosphere; Sealed vessel;99%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

tetramethylstannane
594-27-4

tetramethylstannane

1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

Conditions
ConditionsYield
With C31H33INPPd In N,N-dimethyl-formamide at 80℃; for 24h; Stille coupling;98%
With iodophenylbis(triphenylphosphine)palladium In N,N,N,N,N,N-hexamethylphosphoric triamide at 70℃; for 0.5h;87%
tetramethylstannane
594-27-4

tetramethylstannane

benzoyl chloride
98-88-4

benzoyl chloride

acetophenone
98-86-2

acetophenone

Conditions
ConditionsYield
Pd(phenylimino)acenaphthene dimethyl fumarate In N,N-dimethyl-formamide at 50℃; for 16h;98%
With bis(η3-allyl-μ-chloropalladium(II)) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.333333h; Mechanism;85%
With N,N,N,N,N,N-hexamethylphosphoric triamide; poly-γ-(diphenylphosphino)propylsiloxane palladium(0) at 65℃; for 20h; Product distribution; other organic halides; also organomagnesium reagents; var. solvents and temp.;85%
With aluminium trichloride In dichloromethane for 20h; Ambient temperature;84%
benzylchlorobis(triphenylphosphine)pa.. In chloroform at 65℃; competition with Me3SnPh; relative reaction rates of benzoyl chloride with organotins;
tetramethylstannane
594-27-4

tetramethylstannane

4-iodo-3-phenyl-1H-isochromen-1-one
118520-78-8

4-iodo-3-phenyl-1H-isochromen-1-one

3-phenyl-4-methyl-1H-isochromen-1-one

3-phenyl-4-methyl-1H-isochromen-1-one

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; copper(l) iodide; dichlorobis(tri-O-tolylphosphine)palladium at 60℃; for 117h;98%
C26H26F3NO7S2

C26H26F3NO7S2

tetramethylstannane
594-27-4

tetramethylstannane

C26H29NO4S

C26H29NO4S

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide for 3h; Stille coupling; Heating;98%
trifluoromethanesulfonic acid 6,10-methano-4-iodo-8,8-dimethyl-1-(toluene-4-sulfonyl)-6,6a,9a,10-tetrahydro-1H-7,9-dioxa-1-azadicyclopenta[a,g]naphthalen-5-yl ester

trifluoromethanesulfonic acid 6,10-methano-4-iodo-8,8-dimethyl-1-(toluene-4-sulfonyl)-6,6a,9a,10-tetrahydro-1H-7,9-dioxa-1-azadicyclopenta[a,g]naphthalen-5-yl ester

tetramethylstannane
594-27-4

tetramethylstannane

4,5,8,8-tetramethyl-6,10-methano-1-(toluene-4-sulfonyl)-6,6a,9a,10-tetrahydro-1H-7,9-dioxa-1-azadicyclopenta[a,g]naphthalene

4,5,8,8-tetramethyl-6,10-methano-1-(toluene-4-sulfonyl)-6,6a,9a,10-tetrahydro-1H-7,9-dioxa-1-azadicyclopenta[a,g]naphthalene

Conditions
ConditionsYield
With lithium chloride; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide Heating;98%
(4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-4-methylcyclopent-2-enone
1268265-30-0

(4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-4-methylcyclopent-2-enone

tetramethylstannane
594-27-4

tetramethylstannane

(4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-enone
1268265-21-9

(4R,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,4-dimethylcyclopent-2-enone

Conditions
ConditionsYield
With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; triphenyl-arsane In 1-methyl-pyrrolidin-2-one at 80℃; for 6h; Stille coupling; Inert atmosphere;98%
tetramethylstannane
594-27-4

tetramethylstannane

A

methanethiosulfonic acid S-methyl ester
2949-92-0

methanethiosulfonic acid S-methyl ester

B

trimethyltin sulfate

trimethyltin sulfate

Conditions
ConditionsYield
With sulfur dioxide 60°C, liq. SO2;A n/a
B 97%
With SO2 60°C, liq. SO2;A n/a
B 97%
tetramethylstannane
594-27-4

tetramethylstannane

boron tribromide
10294-33-4

boron tribromide

dimethylboron bromide
5158-50-9

dimethylboron bromide

Conditions
ConditionsYield
dropping Sn(CH3)4 to BBr3 for 1 h at -50°C (vigorous react.); slow warming, then short boiling under reflux; distn.;97%
tetramethylstannane
594-27-4

tetramethylstannane

phenyltin trichloride
1124-19-2

phenyltin trichloride

methylphenyltin(IV) dichloride
15649-26-0

methylphenyltin(IV) dichloride

Conditions
ConditionsYield
In neat (no solvent) byproducts: (CH3)3SnCl; (N2); cooling of PhSnCl3 in Schlenk flask to 0°C; addn. dropwise of SnMe4 with stirring; stirring for 0.5 h ((J. Org. Chem. 33 (1968) 1119); pumping under vac. at room temp. for several hs; GS-MS;97%
bis(benzonitrile)palladium(II) dichloride
15617-18-2, 39958-10-6, 14220-64-5

bis(benzonitrile)palladium(II) dichloride

1,4-di(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabutadiene

1,4-di(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabutadiene

tetramethylstannane
594-27-4

tetramethylstannane

[(2,6-iPrC6H3NC(Me)C(Me)N-2,6-iPrC6H3)Pd(CH3)(Cl)]

[(2,6-iPrC6H3NC(Me)C(Me)N-2,6-iPrC6H3)Pd(CH3)(Cl)]

Conditions
ConditionsYield
In dichloromethane under N2 atm. to soln. (PhCN)2PdCl2 in CH2Cl2 at -40°C Me4Sn was added and stirred at -40°C for 1 h and at -30°C for 1.5 h,soln. bisimine ligand in CH2Cl2 was added at -30°C, stirred for 30 min, warmed to room temp., 5 h; soln. was filtered and concd., hexane was added, ppt. was washed with ether and dried in vacuo overnight;97%
tetramethylstannane
594-27-4

tetramethylstannane

bis(fluorosulfonyl)amide
14984-73-7

bis(fluorosulfonyl)amide

trimethyltin(IV) di(fluorosulfonyl)amide
7240-46-2

trimethyltin(IV) di(fluorosulfonyl)amide

Conditions
ConditionsYield
In dichloromethane N2 atm.; equimolar ratio, refluxing (4 h); evapn.; elem. anal.;97%

594-27-4Relevant articles and documents

Craig, P. J.,Rapsomanikis, S.

, p. L19 - L22 (1983)

Kroll et al.

, p. 313,314, 318 (1971)

Polysulfonylamine XXXV. Synthese, Roentgenstrukturanalysen und hochaufgeloeste Festkoerper-NMR-Spektren der ionischen Organozinn(IV)-dimesylamide und 2

Blaschette, Armand,Hippel, Ilona,Krahl, Juergen,Wieland, Elke,Jones, Peter G.,Sebald, Angelika

, p. 279 - 297 (1992)

(4) was prepared by treating Me3SnN(SO2Me)2 (1) with liquid ammonia; single crystals suitable for X-ray diffraction were grown from a solution in liquid ammonia by slow evaporation of the solvent at -42 deg C. 2 (5) was obtained from dimethyl sulfoxide and Me2Sn2 or 1 in refluxing CCl4, the co-product in the latter case being SnMe4.The crystallographic data at -95 deg C are for 4: monoclinic, space group P21/c, a 650.3(2), b 1464.7(3), c 1479.6(4) pm, β 94.63(2) deg, U 1.4046 nm3, Z=4; for 5: triclinic, space group P, a 818.3(2), b 986.6(2), c 1119.9(3) pm, α 79.10(2), β 77.51(2), γ 77.58(2) deg, U 0.8524 nm3, Z=1.The structure refinement of 4 was based on 3092 reflections with F>4?(F) to give R=0.018.For 5, refinement using 3579 reflections with F>4?(F) yielded R=0.021.The crystals of both compounds consist of discrete (MeSO2)2N- anions and Me3Sn(NH3)2+ or Me2Sn(DMSO)42+ cations, respectively.The structures of the anions are similar to those observed in other ionic dimesylamides.In the cation of 4, the tin atom has an axially distorted trigonal-bipyramidal environment with apical NH3 molecules (Sn-N 232.8 and 238.3, Sn-C 211.7-212.4 pm, N-Sn-N 179.2, C-Sn-C 118.1-122.1, N-Sn-C 88.0-91.3 deg).The tin atom in the centrosymmetric cation of 5 displays trans-octahedral geometry with four DMSO molecules bonded through their oxygen atoms (Sn-C 211.4, Sn-O 219.9 and 221.4 pm, (O-Sn-O)cis 88.9 and 91.1, O-Sn-C 86.8-93.2 deg).The oxygen centres of the sulfoxide ligands are sp2-hybridized with Sn-O-S 121.8 and 123.1 deg, S-O 154.4 and 155.4 pm. 5 is the first example of a structurally characterized tin(IV)-sulfoxide complex in which four sulfoxide ligands are coordinated to a single tin centre. 13C, 15N and 119Sn CP/MAS NMR spectra of solid 4 and 5 agree very well with the X-ray diffraction results.In both cases, the isotropic 119Sn chemical shifts and their tensorial properties support the nearest-neighbours-environment as shown by crystallography.The slight inequivalences of the NH3 and DMSO ligands, respectively, are mirrored in the 15N and 13C CP/MASS spectra of 4 and 5.The 119Sn CP/MAS spectrum of 4 is complicated by the simultaneous presence of scalar and quadrupolar coupling of two inequivalent 14N nuclei with 119Sn.

Vibrational Spectra and Normal Coordinate Calculations for Trimethylstannane

Imai, Yoshika,Aida, Koyo

, p. 999 - 1002 (1982)

The infrared and Raman spectra of trimethylstannane and its deuterated analogues were obtained.Assignments for all the fundamentals except internal torsions were made and normal coordinate calculations were carried out to confirm the proposed assignments.

Cullen,W.R. et al.

, p. 406 - 413 (1965)

Cotton et al.

, p. 253 (1966)

The first 1,1′-Digallylferrocene and a rodlike, polymeric donor-acceptor complex: Synthesis, properties, and structure of [Fe(η5-C5H4GaMe2)2] n and [Fe(η5-C5H4GaMe2)2(C 12H8N2)]n

Althoff, Alexander,Jutzi, Peter,Lenze, Norman,Neumann, Beate,Stammler, Anja,Stammler, Hans-Georg

, p. 3018 - 3022 (2002)

The reaction of 1,1?-bis(trichlorostannyl)ferrocene with trimethylgallium results in the formation of Fe(C5H4GaMe2)2 (1), the first digallylferrocene. An X-ray crystal structure analysis of 1 reveals a polymeric structure. NMR data confirm a monomeric structure of [1-2 donor] in donor solvents. The reaction of 1 with phenazine results in the formation of the supramolecular polyferrocene [1·phenazine]n. Its rodlike structure is proven by X-ray crystallography.

Group 13 and 14 alkyl derivatives of the imido-nitrido metalloligand [{Ti(η5-C5Me5)(μ-NH)} 3(μ3-N)]

Garcia-Castro, Maria,Martin, Avelino,Mena, Miguel,Yelamos, Carlos

, p. 408 - 416 (2007)

The reactivity of the imido-nitrido trinuclear complex [{Ti- (η5-C5Me5)(μ-NH)}3(μ 3-N)] (1) toward alkyl derivatives of group 13 and 14 elements has been investigated. Treatment of 1 with trialkyl der

Brown, O. R.,Gonzales, E. R.,Wright, A. R.

, p. 369 - 372 (1973)

Fleischmann, M.,Mengoli, G.,Pletcher, D.

, p. 231 - 235 (1973)

Kraus, C. A.,Greer, W. N.

, p. 2568 - 2575 (1925)

The reactivity of metal-metal bonds. II. The tin-manganese bond

Clark,Tsai

, p. 1407 - 1415 (1966)

The reactions of trimethyltinpentacarbonylmanganese with tetrafluoroethylene, trifluoroethylene, chlorotrifluoroethylene, and ethylene are described. Only with tetrafluoroethylene is an adduct, namely, (CH3)3SnCF2CF2Mn(CO)5, obtained, although trimethyltin fluoride and fluorocarbon-carbonylmanganese products are also formed. With trifluoroethylene and chlorotrifluoroethylene, trimethyltin halides and fluorovinylpentacarbonylmanganese compounds are produced, although in the latter case perfluoroacryloylpentacarbonylmanganese, CF2=CFCOMn(CO)5, is a major product. Ethylene does not cleave the Sn-Mn bond, but rather displaces carbon monoxide to form (CH3)3SnMn(CO)4(π-C2H 4). The spectroscopic properties of the new compounds are discussed.

Octahedral Bis(phenoxy-imine)tin(IV) alkyl complexes: Synthesis, characterization, and reactivity toward ionizing species and ethylene

Annunziata, Liana,Pappalardo, Daniela,Tedesco, Consiglia,Pellecchia, Claudio

, p. 1947 - 1952 (2005)

The synthesis of new organotin compounds of the general formula L 2SnR2 (L = N-(3-tert-butylsalicylidene)-2,3,4,5,6- pentafluoroaniline; R = CH3 (1), n-C4H9 (3)) and L′2SnR2 (L′ = Ar-(3-tert- butylsalicylidene)aniline; R = CH3 (2), n-C4H9 (4)) is described herein. The compounds were characterized by 1H, 13C, and 119Sn NMR in solution; in some cases a fluxional behavior was observed by variable-temperature experiments. Characterization by single-crystal X-ray diffraction analysis has been obtained for compounds 1, 2, and 4. The reactivity of the synthesized compounds toward ionizing agents was studied by an NMR-tube reaction. Compounds 2 and 4 underwent an alkyl abstraction reaction with the carbenium salt [C(C6H5) 3]+[B(C6F5)4] . The obtained cationic species exhibited some activity in the oligomerization of ethylene under mild conditions, producing short-chain oligomers, with saturated end groups and methyl branches.

ORGANOMETALLIC COMPOUNDS AND METHODS FOR THE DEPOSITION OF HIGH PURITY TIN OXIDE

-

Paragraph 0103, (2019/02/17)

Disclosed herein are compounds useful for the deposition of high purity tin oxide. Also disclose are methods for the deposition of tin oxide films using such compounds. Such films demonstrate high conformality, high etch selectivity and are optically transparent. Such compounds are those of the Formula as follows R x -Sn-A 4-x wherein: A is selected from the group consisting of (Y a R' z ) and a 3- to 7-membered N- containing heterocyclic group; each R group is independently selected from the group consisting of an alkyl or aryl group having from 1 to 10 carbon atoms; each R' group is independently selected from the group consisting of an alkyl, acyl or aryl group having from 1 to 10 carbon atoms; x is an integer from 0 to 4; a is an integer from 0 to 1; Y is selected from the group consisting of N, O, S, and P; and z is 1 when Y is O, S or when Y is absent and z is 2 when Y is N or P.

A utility for organoleads: Selective alkyl and aryl group transfer to tin

Arias-Ugarte, Renzo N.,Pannell, Keith H.

, p. 1703 - 1708 (2018/02/09)

Me4Pb and Ph4Pb readily transfer methyl or phenyl groups to an equivalent molar ratio of tin(iv) chlorides in the order SnCl4 > MeSnCl3 > Me2SnCl2 > Me3SnCl, often in a selective manner. Me3PbCl and Ph3PbCl specifically transfer a single methyl/phenyl group under the same reaction conditions to produce recovered yields in >75%. Specific transfer of 2 methyl groups from PbMe4 can be achieved at elevated temperatures and/or a 2:1 molar ratio Pb:Sn.

Formation of silicon-carbon bonds by photochemical irradiation of (η5-C5H5)Fe(CO)2SiR3 and (η5-C5H5)Fe(CO)2Me to Obtain R3SiMe

Fortier, Skye,Zhang, Yongqiang,Sharma, Hemant K.,Pannell, Keith H.

, p. 1041 - 1044 (2010/04/25)

Photochemical irradiation of an equimolar mixture of (η5 -C5H5)Fe(CO)2SiR3, FpSiR 3, and FpMe leads to the efficient formation of the silicon-carbon-coupled product R3SiMe, R3 = Me 3, Me2Ph, MePh2, Ph3, ClMe 2, Cl2Me, Cl3, Me2Ar (Ar = C 6H4-p-X, X = F, OMe, CF3, NMe2). Similar chemistry occurs with related germyl and stannyl complexes at slower rates, Si > Ge Sn. Substitution of an aryl hydrogen to form FpSiMe2C6H4-p-X has little effect on the rate of the reaction, whereas progressive substitution of methyl groups on silicon by Cl slows the process. Also, changing FpMe to FpCH2SiMe3 dramatically slows the reaction as does the use of (η5-C 5Me5)Fe(CO)2 derivatives. A mechanism involving the initial formation of the 16e intermediate (η5-C 5H5)Fe(CO)Me followed by oxidative addition of the Fe-Si bond accounts for the experimental results obtained.

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