Tributylstannane → 3-Cycloheptylpropanenitrile

HRID 1085070Notes

Reaction equation

HRID 1085070 reaction equation
Br[CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CCCC[SnH](CCCC)CCCC.[C:22](#[N:25])[CH:23]=[CH2:24].CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[CH:2]1([CH2:24][CH2:23][C:22]#[N:25])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 7855AcrylonitrileHCID 16992Bromocycloheptane

Product 1

HCID 131640453-Cycloheptylpropanenitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Cycloheptylpropionitrile is prepared in this example according to the procedure of Example 1 using a solution of 2-bromocycloheptane (25.57 g; 144.38 mmole); Bu3SnH (50.42 g; 173.26 mmole), acrylonitrile (15.32 g; 288.77 mmole), and AIBN (1.13 g) in toluene (300 ml). Yield is 16 g; mp oil.

Sources & evidence

ORD record
ord-8e7da019e32f41f4baaf4eadfa9ecce2
Source dataset
uspto-grants-1991_04
Patent number
US05008265

Reaction notes

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