Tributyltin Chloride → Tributyl[(phenylsulfanyl)methyl]stannane

HRID 973112Notes

Reaction equation

HRID 973112 reaction equation
[C:1]1([S:7][CH2:8][Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([Sn:14](Cl)([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH3:13].[Cl-].[NH4+]>CCCCCC.C1COCC1.C1COCC1>[C:1]1([S:7][CH2:8][Sn:14]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:10][CH2:11][CH2:12][CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 178506884HCID 178506884, compound

Product 1

HCID 13495644Tributyl[(phenylsulfanyl)methyl]stannane

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21883165Tetrahydrofuran hexaneSolvent

Conditions

Temperature
0 °C

Procedure

Using the apparatus and procedure of Example I, 100 ml. of an approximately one-molar solution of (phenylthio) methyllithium in hexane-THF solvent was added dropwise with stirring to 0.1 mole of tributyltin chloride dissolved in THF. The temperature was maintained by means of an ice bath in the range of from 0° C to 20 C. Following the complete addition over a one-half hour period, the reaction mixture was stirred for 1.5 hours at room temperature and hydrolyzed by pouring into aqueous one-molar ammonium chloride. Extraction from the hydrolyzate with ether solvent and purification by vacuum distillation yielded the desired product, (phenylthiomethyl) tributyltin, b.p. 152°-157° C (0.09 mm). Infrared and proton nuclear magnetic resonance spectral analyses confirmed the assigned structure.

Workup

  1. additionthe complete addition over a one-half hour period
  2. extractionExtraction from the hydrolyzate
  3. customwith ether solvent and purification
  4. distillationby vacuum distillation

Sources & evidence

ORD record
ord-b0a0ce4241424e1ba5a4265a123abb3a
Source dataset
uspto-grants-1977_10
Patent number
US04055413

Reaction notes

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