[C:1](#[N:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[N:19].C([O-])(O)=[O:22].[Na+].OOS([O-])=O.[K+].C(Cl)Cl>CC(C)=O.O>[O:22]1[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]#[N:20])[CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[N:19]
A mixture of 0.1000 g (E)-octadec-9-enedinitrile and 0.2334 g NaHCO3 in 4.0 mL acetone was cooled in an ice water bath. While stirring, a solution of 0.5365 g Oxone® in 4.0 mL water was added in portions during 30 min. The mixture was allowed to warm to room temperature over 18 h, then 200 mL CH2Cl2 and 10 mL water were added to the reaction mixture to afford a clear 2-phase system. The organic phase was dried over Na2SO4 and evaporated to afford 0.10 g of product as a colorless oil.
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