1,10-diiododecane

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of butyllithium (2.84 ml of a 1.6 M solution in hexane, 4.5 mmol) in dry tetrahydrofuran (THF, 45 ml) was added dropwise a solution of acetylene 9 (500 mg, 1.13 mmol) in dry THF (10 ml) at -40° C. The reaction mixture was then allowed to warm up to -10° C. and stirred for 1 h. At his temperature, a solution of 1,10-diiododecan (2.15 g, 5.4 mmol) in dry THF (5 ml) was added in one portion. The cooling bath was removed and the reaction mixture was stirred at room temperature for 15 h. Then, the solution was diluted with 100 ml of ether and was washed with water (6×30 ml), dried, filtered and concentrated to an oil. The residue was purified by flash chromatography (hexane:acetone, 96:4), followed by preparative thin-layer chromatography (TLC) to give 208 mg, 26% of compound 10 (n=10) The cooling bath was removed the reaction mixture was stirred at room temperature for 15 h Then, the solution was diluted with 100 ml of ether was washed with water (6×30 ml) dried filtered concentrated to an oil The residue was purified by flash chromatography (hexane:acetone, 96:4)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,10-Diiododecane (mmol) was added to a solution (30 mL) of isoquinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in a 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.07 (1H, d, C1-H), 8.78 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.36 (1H, d, C7-H), 8.26 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.69 (2H, t, C′1-CH2), 2.0 (2H, m, C′2-CH2), 1.15-1.50 (6H, m, C′3-5-CH2). The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 92% yield

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,10-Diiododecane (mmol) was added to a solution (30 mL) of isoquinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in a 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.07 (1H, d, C1-H), 8.78 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.36 (1H, d, C7-H), 8.26 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.69 (2H, t, C′1-CH2), 2.0 (2H, m, C′2-CH2), 1.15-1.50 (6H, m, C′3-5-CH2). The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 92% yield

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,10-Diiododecane (mmol) was added to a solution (30 mL) of dry quinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in a 91% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.53 (1H, d, C2-H), 9.29 (1H, d, C3-H), 8.61 (1H, d, C8-H), 8.50 (1H, d, C4-H), 8.29 (1H, t, C7-H), 8.18 (1H, t, C5-H), 8.06 (1H, d, C6-H), 5.04 (2H, t, C′1-CH2), 1.96 (2H, m, C′2-CH2), 1.32 (6H, m, C′3-5-CH2); 13C NMR (75 MHz, DMSO-D6) δ 149.5, 147.4, 137.4, 135.6, 130.7, 129.9, 129.7, 122.1, 118.9, 57.3, 29.5, 28.9, 28.5, 25.7. The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 91% yield

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,10-Diiododecane (mmol) was added to a solution (30 mL) of dry quinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in a 91% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.53 (1H, d, C2-H), 9.29 (1H, d, C3-H), 8.61 (1H, d, C8-H), 8.50 (1H, d, C4-H), 8.29 (1H, t, C7-H), 8.18 (1H, t, C5-H), 8.06 (1H, d, C6-H), 5.04 (2H, t, C′1-CH2), 1.96 (2H, m, C′2-CH2), 1.32 (6H, m, C′3-5-CH2); 13C NMR (75 MHz, DMSO-D6) δ 149.5, 147.4, 137.4, 135.6, 130.7, 129.9, 129.7, 122.1, 118.9, 57.3, 29.5, 28.9, 28.5, 25.7. The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 91% yield

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,10-Diiododecane (mmol) was added to a solution (30 mL) of dry pyridine, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in a 90% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.10 (2H, d, C2&C6-H), 8.63 (1H, t, C4-H), 8.19 (2H, t, C3&C5-H), 4.60 (2H, t, C′1-CH2), 1.89 (2H, m, C′2-CH2), 1.24 (6H, m, C′3-5-CH2); 13C NMR (75 MHz, DMSO-D6) δ 145.3, 144.5, 127.9, 60.6, 30.6, 28.8, 28.1, 25.2. The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 90% yield

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of butyllithium (2.84 ml of a 1.6M solution in hexane, 4.5 mmol) in dry tetrahydrofuran (THF, 45 ml) was added dropwise a solution of acetylene 9 (500 mg, 1.13 mmol) in dry THF (10 ml) at -40° C. The reaction mixture was then allowed to warm up to -10° C. and stirred for 1 h. At this temperature, a solution of 1,10-diiododecan (2.15 g, 5.4 mmol) in dry THF (5 ml) was added in one portion. The cooling bath was removed and the reaction mixture was stirred at room temperature for 15 h. Then, the solution was diluted with 100 ml of ether and was washed with water (6×30 ml), dried, filtered and concentrated to an oil. The residue was purified by flash chromatography (hexane:acetone, 96:4), followed by preparative thin-layer chromatography (TLC) to give 208 mg, 26% of compound 10 (n=10) The cooling bath was removed the reaction mixture was stirred at room temperature for 15 h Then, the solution was diluted with 100 ml of ether was washed with water (6×30 ml) dried filtered concentrated to an oil The residue was purified by flash chromatography (hexane:acetone, 96:4)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound is prepared from 4-benzyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine and 1,10-diiododecane according to the procedure of Example 5.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound is prepared from 4-benzyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine and 1,10-diiododecane according to the procedure of Example 5.

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of butyllithium (2.84 ml of a 1.6 M solution in hexane, 4.5 mmol) in dry tetrahydrofuran (THF, 45 ml) was added dropwise a solution of acetylene 9 (500 mg, 1.13 mmol) in dry THF (10 ml) at -40° C. The reaction mixture was then allowed to warm up to -10° C. and stirred for 1 h. At his temperature, a solution of 1,10-diiododecan (2.15 g, 5.4 mmol) in dry THF (5 ml) was added in one portion. The cooling bath was removed and the reaction mixture was stirred at room temperature for 15 h. Then, the solution was diluted with 100 ml of ether and was washed with water (6×30 ml), dried, filtered and concentrated to an oil. The residue was purified by flash chromatography (hexane:acetone, 96:4), followed by preparative thin-layer chromatography (TLC) to give 208 mg, 26% of compound 10 (n=10) The cooling bath was removed the reaction mixture was stirred at room temperature for 15 h Then, the solution was diluted with 100 ml of ether was washed with water (6×30 ml) dried filtered concentrated to an oil The residue was purified by flash chromatography (hexane:acetone, 96:4)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,10-Diiododecane (mmol) was added to a solution (30 mL) of isoquinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in a 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.07 (1H, d, C1-H), 8.78 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.36 (1H, d, C7-H), 8.26 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.69 (2H, t, C′1-CH2), 2.0 (2H, m, C′2-CH2), 1.15-1.50 (6H, m, C′3-5-CH2). The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 92% yield

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,10-Diiododecane (mmol) was added to a solution (30 mL) of dry quinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in a 91% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.53 (1H, d, C2-H), 9.29 (1H, d, C3-H), 8.61 (1H, d, C8-H), 8.50 (1H, d, C4-H), 8.29 (1H, t, C7-H), 8.18 (1H, t, C5-H), 8.06 (1H, d, C6-H), 5.04 (2H, t, C′1-CH2), 1.96 (2H, m, C′2-CH2), 1.32 (6H, m, C′3-5-CH2); 13C NMR (75 MHz, DMSO-D6) δ 149.5, 147.4, 137.4, 135.6, 130.7, 129.9, 129.7, 122.1, 118.9, 57.3, 29.5, 28.9, 28.5, 25.7. The resulting precipitate was filtered the product washed five times with dry diethyl ether The resulting yellow solid was isolated in a 91% yield