Br[C:2]12[CH2:11][C:6]3([CH3:12])[CH2:7][CH:8]([CH2:10][C:4]([CH3:13])([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:14](#[N:17])[CH:15]=[CH2:16].C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1.CCOCC.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>[CH3:12][C:6]12[CH2:7][CH:8]3[CH2:10][C:4]([CH3:13])([CH2:3][C:2]([CH2:16][CH2:15][C:14]#[N:17])([CH2:9]3)[CH2:11]1)[CH2:5]2A solution of 1-bromo-3,5-dimethyladamantane (1.0 g, 4.11 mmol), acrylonitrile (436 mg, 8.22 mmol) and 1,1′-azobis(cyclohexanecarbonitrile) (50 mg, 0.21 mmol) in dry toluene (12 mL) was treated with tri-n-butyltin hydride (1.44 g, 4.93 mmol) at room temperature, refluxed for 3.5 h, cooled, diluted with ether (30 mL), washed with 0.2-M NH4OH (30 mL), water (10 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography [SiO2, CH2Cl2-hexane (0:100 to 100:0)] to give the product (771 mg, 86%) as a colourless oil: IR νmax (liquid film)/cm−1 2899, 2841, 2247, 1545 and 1359; NMR δH (400 MHz, CDCl3) 0.81 (6H, s), 1.0-1.2 (6H, m), 1.25-1.35 (6H, m), 1.53 (2H, t, J 4.2 Hz), 2.05-2.10 (1H, m) and 2.27 (2H, tJ 4.2 Hz).
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