Iodine → 1-Iodo-nonadeca-1,8,10-triyne
Reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][C:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[I:20]I>C1COCC1>[I:20][C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][C:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Nonadeca-1,8,10-triyne (0.802 g, 3.133 mmol) and anhydrous THF (96 mL) was cooled to −78° C. in a dry flask under nitrogen. LiN[Si(CH3)]2 (LHMDS) in THF (3.76 mmol) was added to the reaction mix slowly via dry syringe. In a separate flask I2 (9.55 g, 3.76 mmol) was dissolved in dry THF (20 mL). The iodine solution was added dropwise to the nonadeca-1,8,10-triyne solution until reaction completion (notably becoming orange-red). The reaction was stirred for 30 min, and slowly warmed to room temperature. The reaction was extracted with diethyl ether and 1M K2S2O3. The organic phase was dried over anhydrous MgSO4, and concentrated by evaporation to yield 1-iodo-nonadeca-1,8,10-triyne (0.93 g, 2.45 mmol). GC/MS showed no starting material remaining 79% yield; 1H NMR (CDCl3) δ 2.15-2.33 (m, 6H, CH2—C≡C), 1.48 (m, 6H, CH2—C—C≡C), 1.33-1.39 (m, 2H, CH2—CH2—CH3), 1.28 (m, 10H, C—CH2—C), 0.85 (t, 3H, CH3).