IODOHYDRINS, IODO ETHERS, AND EPOXIDES
1321
1.79–1.84 (m, 2H), 3.23–3.29 (m, 2H), 3.40 (sept, 1H, J ¼ 6.1 Hz), 3.44–3.53 (m, 3H),
4.89–4.95 (m, 1H). 13C NMR (100 MHz, CDCl3) d 19.0, 20.2, 23.7, 27.6, 28.9, 33.5,
36.8, 38.9, 43.8, 61.8, 63.8, 69.1, 75.6, 105.2. IR (cmꢁ1, neat) n 2936, 2845, 1155, 740,
661.
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2-(7-tert-Butoxy-6-iodo-3,7-dimethyl-octyloxy)-tetrahydro-pyran 11(d). H
NMR (400 MHz, CDCl3) d 1.03 (s, 3H), 1.11 (s, 9H), 1.19–1.23 (m, 2H), 1.26 (s,
6H), 1.37–1.43 (m, 2H), 1.56–1.65 (m, 7H), 1.77–1.83 (m, 2H), 3.23–3.27 (m, 2H),
3.43–3.57 (m, 3H), 4.91–4.96 (m, 1H). 13C NMR (100 MHz, CDCl3) d 19.3, 21.1,
27.9, 29.2, 30.9, 33.6, 36.8, 38.9, 43.5, 61.1, 64.0, 76.7, 103.1. IR (cmꢁ1, neat) n
2921, 2805, 1441, 1137, 742, 667.
2-(3,7-Dimethyl-oct-6-enyloxy)-tetrahydro-pyran oxide 11(e). 1H NMR
(400 MHz, CDCl3) d 1.00 (s, 3H), 1.16–1.20 (m, 2H), 1.23 (s, 6H), 1.34–1.37 (m,
2H), 1.55–1.61 (m, 7H), 1.72–1.79 (m, 2H), 2.69–2.78 (m, 1H), 3.20–3.26 (m, 2H),
3.39–3.51 (m, 2H), 4.87–4.93 (m, 1H). 13C NMR (100 MHz, CDCl3) d 19.1, 20.3,
27.5, 28.7, 33.1, 36.4, 38.2, 43.1, 54.3, 60.2, 63.8, 65.1, 100.8. IR (cmꢁ1, neat) n
2919, 2801, 1025, 740, 666.
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1-Iodo-3,7-dimethyl-3-(tetrahydro-pyran-2-yloxy)-oct-6-en-2-ol 12(a). H
NMR (400 MHz, CDCl3) d 1.29 (s, 3H), 1.36–1.42 (m, 2H), 1.56–1.62 (m, 4H), 1.68
(s, 6H), 1.75–1.89 (m, 4H), 2.35 (bs, 1H, D2O exchangeable), 3.16–3.26 (m, 2H),
3.58–3.65 (m, 2H), 4.01 (dd, 1H, J1 ¼ 8.8, J2 ¼ 3.6 Hz), 4.90–4.96 (m, 1H),
5.18–5.23 (m, 1H). 13C NMR (100 MHz, CDCl3) d 9.0, 18.7, 19.3, 25.3, 28.0, 33.6,
34.8, 62.5, 71.5, 86.1, 93.6, 124.8, 132.4. IR (cmꢁ1, neat) n 3442 (br), 2951, 1626,
1430, 1157, 758, 612.
2-[1-(1-Ethoxy-2-iodo-ethyl)-1,5-dimethyl-hex-4-enyloxy]-tetrahydro-pyran
12(b). 1H NMR (400 MHz, CDCl3) d 1.09 (t, 3H, J ¼ 7.0), 1.28 (s, 3H), 1.34–1.41
(m, 2H), 1.52–1.59 (m, 4H), 1.65 (s, 6H), 1.73–1.84 (m, 4H), 3.14–3.23 (m, 2H),
3.28–3.34 (m, 2H), 3.53–3.61 (m, 2H), 4.00 (dd, 1H, J1 ¼ 8.8, J2 ¼ 3.6 Hz),
4.88–4.93 (m, 1H), 5.15–5.21 (m, 1H). 13C NMR (100 MHz, CDCl3) d 9.1, 15.2,
18.9, 20.3, 26.6, 28.5, 34.6, 35.3, 60.2, 62.9, 72.1, 86.9, 93.8, 125.7, 134.1. IR (cmꢁ
1, neat) n 2989, 2866, 1645, 1442, 1134, 777, 638.
2-[1-(2-Iodo-1-isopropoxy-ethyl)-1,5-dimethyl-hex-4-enyloxy]-tetrahydro-
1
pyran 12(c). H NMR (400 MHz, CDCl3) d 1.10 (d, 3H, J ¼ 5.4 Hz), 1.19 (d, 3H,
J ¼ 5.4 Hz), 1.30 (s, 3H), 1.37–1.44 (m, 2H), 1.57–1.63 (m, 4H), 1.70 (s, 6H),
1.76–1.89 (m, 4H), 3.19–3.27 (m, 2H), 3.47 (sept, 1H, J ¼ 6.1 Hz), 3.60–3.67 (m,
2H), 4.05 (dd, 1H, J1 ¼ 8.8, J2 ¼ 3.6 Hz), 4.91–4.96 (m, 1H), 5.20–5.26 (m, 1H).
13C NMR (100 MHz, CDCl3) d 9.0, 18.7, 19.3, 23.0, 25.3, 28.0, 33.6, 34.8, 62.5,
66.7, 71.5, 87.3, 95.4, 125.8, 134.8. IR (cmꢁ1, neat) n 2956, 1629, 1143, 760, 616.
2-[1-(1-tert-Butoxy-2-iodo-ethyl)-1,5-dimethyl-hex-4-enyloxy]-tetrahydro-
1
pyran 12(d). H NMR (400 MHz, CDCl3) d 1.10 (s, 9H), 1.27 (s, 3H), 1.34–1.40 (m,
2H), 1.53–1.59 (m, 4H), 1.65 (s, 6H), 1.71–1.84 (m, 4H), 3.13–3.21 (m, 2H), 3.53–3.63
(m, 2H), 4.01 (dd, 1H, J1 ¼ 8.8, J2 ¼ 3.6 Hz), 4.87–4.92 (m, 1H), 5.15–5.21 (m, 1H).
13C NMR (100 MHz, CDCl3) d 9.1, 18.7, 19.4, 25.3, 28.1, 30.1, 33.6, 34.8, 62.5, 71.5,
86.1, 95.2, 124.8, 134.1. IR (cmꢁ1, neat) n 2943, 1631, 1415, 1109, 761, 614.