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14. A 250 mL three-neck flask equipped with an internal
thermometer, condenser, and pressure-equalizing addition
funnel was flame dried under nitrogen and then charged
with 1.17 g (8.5 mmol) of finely ground, anhydrous K2CO3
and 100 mL of dry DMF. After thorough degassing with
N2, the reaction mixture was stirred and heated to 150 °C.
A solution of 0.38 g (4.0 mmol) of 1,2-ethanedithiol and
2.20 g (4.0 mmol) of 4,9-dithiadodecane-1,12-di-p-toluene-
sulfonate in 50 mL of dry DMF was added dropwise
slowly over 8 h. The reaction mixture was then stirred at
150 °C for an additional 12 h. The mixture was cooled to
room temperature, filtered, and the filtrate concentrated in
vacuo. The residue was purified by flash chromatography
on silica gel using 5% ethyl acetate in hexanes to give
0.23 g compound 17 as a white crystalline solid mp 62.0–
62.5 °C (uncorrected); 1H NMR (CDCl3, 300 MHz) d:
1.78–1.82 (m, 4H), 1.95 (quintet, J = 6.96 Hz, 4H), 2.62–
2.72 (m, 8H); 13C NMR (CDCl3, 75 MHz) d: 27.91, 29.93,
30.11, 31.65, 32.24; m/z (positive ion electrospray): 343.0,
345.0 (M+Ag)+.
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