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L. SU ET AL.
21.5, 24.4, 30.2, 31.2, 50.4, 50.6, 62.6, 101.3, 102.4. MS (ESI) (m=z): 281 (M þ Hþ,
100). Anal. calcd. for C10H17IO: C, 42.87; H, 6.12. Found: C, 42.55; H, 6.30.
2,3-Diiodoprop-2-en-1-ol (4a). Yield: 88%. IR (KBr) nmax: 3205, 2930, 1603,
1038 cmꢃ1
.
1H NMR (400 MHz, CDCl3): d 2.33 (t, J ¼ 6.3 Hz, 1H, OH), 4.30
(d, J ¼ 6.3 Hz, 2H, H-1), 7.06 (s, 1H, H-3). 13C NMR (100 MHz, CDCl3): d 70.7
(C-1), 79.9 (C-3), 104.1 (C-2). MS (ESI) (m=z): 311 (M þ Hþ, 100). Anal. calcd. for
C3H4I2O: C, 11.63; H, 1.30. Found: C, 11.23; H, 1.57.
2,3-Diiodo-3-phenylprop-2-en-1-ol (4b). Yield: 71%. IR (KBr) nmax: 3178,
2924, 1597, 1440, 1022, 683 cmꢃ1 1H NMR (400 MHz, CDCl3): d 2.40 (s, 1H,
.
OH), 4.61 (s, 2H, H-1), 7.20–7.45 (m, 5H, Ph-H). 13C NMR (100 MHz, CDCl3): d
75.9 (C-1), 95.9, 105.0, 128.0 (2C), 128.4 (2C), 128.5, 147.1. MS (ESI) (m=z): 387
(M þ Hþ, 100). Anal. calcd. for C9H8I2O: C, 28.01; H, 2.09. Found: C, 28.12; H, 2.03.
2,3-Diiodohex-2-en-1-ol (4c). Yield: 85%. IR (KBr) nmax: 3206, 2936, 1601,
1032 cmꢃ1. 1H NMR (400 MHz, CDCl3): d 1.01 (d, J ¼ 7.4 Hz, 3H, CH3), 1.62 (sep,
J ¼ 7.4 Hz, 2H, H-5), 2.00–2.10 (br s, 1H, OH), 2.74 (t, J ¼ 7.4 Hz, 2H, H-4), 4.47
(s, 2H, H-1). 13C NMR (100 MHz, CDCl3): d 12.8, 21.3, 52.2, 76.6 (C-1), 101.7,
103.6. MS (ESI) (m=z): 353 (M þ Hþ, 100). Anal. calcd. for C6H10I2O: C, 20.48; H,
2.86. Found: C, 20.21; H, 2.95.
2,3-Diiodooct-2-en-1-ol (4d). Yield: 80%. IR (KBr) nmax: 3226, 3062, 2925,
1
1611, 1037 cmꢃ1. H NMR (400 MHz, CDCl3): d 0.92 (t, J ¼ 7.0 Hz, 3H, CH3),
1.30–1.38 (m, 6H), 1.52–1.62 (m, 2H), 2.50–2.58 (br s, 1H, OH), 3.95 (t, J ¼ 6.8 Hz,
1H, H-3), 7.03 (s, 1H, H-1). 13C NMR (100 MHz, CDCl3): d 14.0, 22.5, 24.3, 31.6,
36.6, 76.1 (C-3), 78.6 (C-1), 113.1 (C-2). MS (ESI) (m=z): 381 (M þ Hþ, 100). Anal.
calcd. for C8H14I2O: C, 25.29; H, 3.71. Found: C, 24.86; H, 3.89.
2,3-Diiodobut-2-en-1-ol (4e). Yield: 87%. IR (KBr) nmax: 3202, 2944, 1632,
1
1035 cmꢃ1. H NMR (400 MHz, CDCl3): d 2.17 (s, 1H, OH), 2.68 (s, 3H, CH3),
4.44 (s, 2H, CH2). 13C NMR (100 MHz, CDCl3): d 40.1, 76.6 (C-1), 95.1, 102.6.
MS (ESI) (m=z): 325 (M þ Hþ, 100). Anal. calcd. for C4H6I2O: C, 14.83; H, 1.87.
Found: C, 14.91; H, 1.85.
3,4-Diiodo-2-methylbut-3-en-2-ol (4f). Yield: 18%. IR (KBr) nmax: 3231,
1
3060, 2922, 1653, 1035 cmꢃ1. H NMR (400 MHz, CDCl3): d 1.64 (s, 6H, 2 ꢂ CH3),
7.22 (s, 1H, H-4). 13C NMR (100 MHz, CDCl3): d 28.9, 29.7, 72.0 (C-2), 114.2 (C-3),
116.8 (C-4). MS (ESI) (m=z): 339 (M þ Hþ, 100). Anal. calcd. for C5H8I2O: C, 17.77;
H, 2.39. Found: C, 17.43; H, 2.61.
1,2-Diiodo-3-methylpent-1-en-3-ol (4g). Yield: 15%. IR (KBr) nmax: 3233,
3067, 2920, 1646, 1033 cmꢃ1. 1H NMR (400 MHz, CDCl3): d 0.99 (t, J ¼ 7.4 Hz, 3H,
CH3), 1.60 (s, 3H, CH3), 1.83 (dq, J ¼ 14.3, 7.4 Hz, 1H, H-4), 2.13 (dq, J ¼ 14.3,
7.4 Hz, 1H, H-4), 2.25 (s, 1H, OH), 7.27 (s, 1H, H-1). 13C NMR (100 MHz, CDCl3):
d 7.8, 28.1, 34.0, 72.3 (C-3), 78.3 (C-2), 117.0 (C-1). MS (ESI) (m=z): 353 (M þ Hþ,
100). Anal. calcd. for C6H10I2O: C, 20.48; H, 2.86. Found: C, 20.41; H, 2.75.
1,2-Diiodo-4-methylpent-1-en-3-ol (4h). Yield: 39%. IR (KBr) nmax: 3428,
1
3062, 2959, 1717, 1037 cmꢃ1. H NMR (400 MHz, CDCl3): d 0.91 (d, J ¼ 6.8 Hz,
3H, CH3), 1.18 (d, J ¼ 6.6 Hz, 3H, CH3), 1.87–1.93 (m, 1H, H-4), 2.36 (s, 1H, OH),
3.56 (d, J ¼ 9.0 Hz, 1H, H-3), 7.11 (s, 1H, H-1). 13C NMR (100 MHz, CDCl3): d