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chromatography (eluent: pentane/acetone 70:1) to afford 3ac (1.38 g,
3.9 mmol) as a colorless oil.
Method 2: To a solution of 1b (1.035 mg, 5 mmol) in dichloro-
methane (10 mL) was added cyclohexene 2a (507 mL, 5 mmol) then
sodium tosylate (1.5 g, 7.7 mmol). The resulting suspension was
stirred vigorously at room temperature. After 5 min of stirring,
BF3·Et2O (3.2 mL, 25 mmol) was then added dropwise. The reaction
mixture stirred for further 4 h before Et2O and H2O were added. The
organic phase was washed with aqueous HCl (2n) and dried over
Na2SO4. After the solvent had been removed in vacuo, the crude was
purified by flash chromatography (eluent: pentane/acetone 70:1) to
afford 3ac (1.5 g/4.24 mmol) as a colorless oil.
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3
3
1H NMR: d = 7.80 (d, J(H,H) = 8.1, 2H), 7.35 (d, J(H,H) = 8.1,
2H), 4.49 (ddd, 3J(H,H) = 6.6, 3J(H,H) = 6.6, 3J(H,H) = 3.6, 1H), 3.29
3
3
3
(ddd, J(H,H) = 6.9, J(H,H) = 6.9, J(H,H) = 4.2, 1H), 2.44 (s, 3H),
2.22 (m, 1H), 2.03 (m, 1H), 1.69–1.65 (m, 3H), 1.48–1.44 ppm (m,
3H). 13C NMR: d = 145.4, 134.0, 130.9 (q, 1J(C,F) = 306), 130.2, 128.3,
80.7, 45.9, 30.4, 30.1, 23.3, 21.9, 21.8 ppm. 19F NMR: d = À40.06 ppm
(s). Elemental analysis calcd (%) for C14H17F3O3S2 : C 47.45, H 4.83, S
18.09; found: C 47.43, H 4.87, S 17.93.
Received: June 23, 2009
Revised: July 20, 2009
Published online: October 6, 2009
Keywords: alkenes · alkynes · electrophilic addition · fluorine ·
.
trifluoromethanesulfanylamides
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