LETTER
Alkyliodonium Ylide
2565
(12) Adam, W.; Gogonas, E. P.; Hadjiarapoglou, L. P. J. Org.
Chem. 2003, 68, 9155.
(13) Adam, W.; Gogonas, E. P.; Hadjiarapoglou, L. P. Eur. J.
Org. Chem. 2003, 1064.
References
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(14) Representative Experimental Procedure.
Synthesis of 3a: A suspension of iodonium ylide 1 (1.0 g,
2.0 mmol) and MeI (2.0 mL) in MeCN (10.0 mL) was stirred
(exclusion of light) at 25 °C for 24 h. The solvent was
evaporated (30 °C at 10 Torr) and the residue was
chromatographed on flash silica gel (CH2Cl2 as eluent) to
yield 0.49 g (56%) of iodide 3a as white crystals, mp 158–
160 °C (lit20 164–165 °C). 1H NMR (250 MHz, CDCl3): d =
2.52 (s, 3 H), 7.57–7.63 (m, 4 H), 7.71–7.77 (m, 2 H), 8.11–
8.15 (m, 4 H). 13C NMR (62.5 MHz, CDCl3): d = 27.1, 73.9,
128.6, 132.3, 134.3, 135.1.
Synthesis of 7: A suspension of iodonium ylide 1 (1.00 g,
2.0 mmol), norbornene (1.00 g, 10.0 mmol), and MeI (2.0
mL) in dry CH2Cl2 (10.0 mL) was stirred (exclusion of light)
at 25 °C for 24 h. The solvent was evaporated (30 °C at 10
Torr) and the residue was chromatographed on flash silica
gel (CH2Cl2 as eluent) to yield 0.43 g (46%) of exo-iodide 7
as white crystals, mp 149–151 °C. IR (KBr): 2960, 2900,
2860, 1440, 1330, 1180, 1150, 1125, 1075, 790, 780, 750
cm–1. 1H NMR (400 MHz, CDCl3): d = 1.23 (d, J = 10.6 Hz,
2 H), 1.31–1.37 (m, 1 H), 1.51–1.65 (m, 2 H), 1.84 (d, J =
10.6 Hz, 1 H), 2.34 (t, J = 7.1 Hz, 1 H), 2.80 (d, J = 3.4 Hz,
1 H), 3.13 (br s, 1 H), 4.62 (dd, J = 1.9, 7.1 Hz, 1 H), 5.42 (d,
J = 7.1 Hz, 1 H), 7.44–7.48 (m, 4 H), 7.61 (t, J = 7.5 Hz, 2
H), 7.96 (t, J = 7.5 Hz, 4 H). 13C NMR (100 MHz, CDCl3):
d = 32.3 (t), 36.8 (t), 40.3 (d), 44.5 (d), 48.7 (d), 49.7 (d),
93.4 (d), 128.8 (d), 129.0 (d), 129.1 (d), 129.4 (d), 134.1 (d),
134.2 (d), 134.2 (d), 138.8 (s), 140.3 (s). Anal. Calcd for
C20H21IO4S2 (516.4): C, 46.52; H, 4.10; S, 12.42. Found: C,
46.52; H, 4.07; S, 12.39.
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(11) Adam, W.; Bosio, S.; Gogonas, E. P.; Hadjiarapoglou, L. P.
Synthesis 2002, 2084.
Synlett 2004, No. 14, 2563–2565 © Thieme Stuttgart · New York