Oxygen → HCID 86608407, compound

Participants

Reaction Steps

A solution of 13 (2.07 g) in CH2Cl2 (50 mL) was saturated with oxygen gas and a solution of NO2 in CH2Cl2 (0.5 mL, 1.32 M) was added. The reaction was then stirred at room temperature under an oxygen atmosphere for 18 hrs. The solvent was removed in vacuo to afford the crude product [5-(4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)pentyl]triphenylphosphonium iodide (14) as a red oil. This residue was re-dissolved in CH2Cl2 (10 mL) and triturated in ether (200 mL) to give an initial yellow precipitate which congealed into a red oil in a few minutes. The solvents were decanted and the precipitate dissolved in CH2Cl2 and the solvent removed in vacuo to give the product (14) (1.866 g) as a red oil. An aliquot (0.880 g) of 14 was purified by column chromatography on silica gel (20 g). Elution with CH2Cl2 gave some unidentified purple coloured material. Elution with 5% ethanol/CH2Cl2 gave the pure iodide product 14 (0.606 g) as a red oil. 1H NMR δ 7.84-7.68 (15H, m, Ar—H) 3.98 (6H, s, 2x Ar—OMe), 3.65 (2H, m, CH2—P+), 2.40 (2H, t, J=7.5 Hz, Ar—CH2), 2.00 (3H, s, Ar-Me), 1.71 (4H, m, —CH2—), 1.43 (2H, m, —CH2—) ppm. 31P NMR (121.4 MHz) δ 25.47 ppm. Anal. calcd. for C32H36IO4P: C, 59.8; H, 5.7; I, 19.8; P, 4.8. Found: C, 60.0; H, 5.3; I, 19.7; P, 4.7%.

Provenance & Evidence