Tributylstannane → Tributyl(dodec-1-en-1-yl)stannane

HRID 865422Notes

Reaction equation

HRID 865422 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:13]([SnH:17]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16]>N(C(C)(C)C#N)=NC(C)(C)C#N>[CH2:22]([Sn:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[CH:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 698211-Dodecyne

Product 1

HCID 71335010Tributyl(dodec-1-en-1-yl)stannaneYield 96%

Reagents, catalysts & solvents 1

HCID 6547AzobisisobutyronitrileCatalyst

Conditions

Temperature
50 °C

Procedure

A solution of 1-dodecyne (50.0 g), tributyltinhydride (109.4 g), and azobisisobutyronitrile (100 mg) was stirred at 95° C. for 3 hrs. The reaction mixture was cooled to 50° C. and evaporated. The residue was filtered through a column of silica, using hexane as the eluent. The appropriate fractions were collected and evaporated. The residue was dried under vacuum to give 131.7 g (96.0%) of tri-n-butyl-1-dodecenylstannane.

Workup

  1. customevaporated
  2. filtrationThe residue was filtered through a column of silica
  3. customThe appropriate fractions were collected
  4. customevaporated
  5. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-b0ed25edb2cf432caccfa947f8776e60
Source dataset
uspto-grants-1996_10
Patent number
US05565584

Reaction notes

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