Trimethylstannane → 6-(p-Tolylsulfonyl)hexyltrimethylstannane

HRID 971699Notes

Reaction equation

HRID 971699 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:17][SnH:18]([CH3:20])[CH3:19]>C1(C)C=CC=CC=1.CC(C)=O>[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Sn:18]([CH3:20])([CH3:19])[CH3:17])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 12623Trimethylstannane2×HCID 100831785-Hexenyl p-tolyl sulfone

Product 1

HCID 234669216-(p-Tolylsulfonyl)hexyltrimethylstannane

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent2×

Procedure

The procedure described in Example 5 was employed except that 10.1 g (42.5 mmoles) of 5-hexenyl p-tolyl sulfone and 14.0 g (85 mmoles) of trimethyltin hydride were the reactants. The reaction mixture was irradiated for 232 hours. The excess trimethyltin hydride was allowed to evaporate from the reaction mixture under a flow of nitrogen. The unreacted 5-hexenyl p-tolyl sulfone was removed from the reaction mixture by distillation at 1 × 10-3 mm Hg leaving 3.25 g of crude product. Column chromatography of the distillation residue over silica gel, employing toluene and 1% acetone in toluene as eluents, afforded an oil, 6-(p-tolylsulfonyl)hexyltrimethylstannane. The presence of both the sulfonyl and trimethyltin moieties was indicated by the strong infrared absorption bands at 1315 cm-1, 1300 cm-1, 1285 cm-1 and 1140 cm-1 (--SO2 --) and 760 cm-1 [(CH3)3Sn--]. NMR showed the following:

Workup

  1. customThe reaction mixture was irradiated for 232 hours
  2. customto evaporate from the reaction mixture under a flow of nitrogen
  3. customThe unreacted 5-hexenyl p-tolyl sulfone was removed from the reaction mixture by distillation at 1 × 10-3 mm Hg
  4. customleaving 3.25 g of crude product

Sources & evidence

ORD record
ord-68589715b4a74045bc6d5ec1ad801d96
Source dataset
uspto-grants-1979_07
Patent number
US04160846

Reaction notes

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