SOME SPECIAL FEATURES OF HYDROALUMINATION-IODINATION
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Table 3. IR and 1Н NMR spectra of iodoalkenediols IIа–IIj, IIIа–IIId, IIIg and allene alcohols IVg, IVh
Comp. no.
IR spectrum
3300–3500 (OH), 1630 (HC=CI), 1050 (CDCl3): 2.6 br.s (2Н, С1ОН, С4ОН), 4.26 d (2Н, H1, J 1.2), 4.28 d.d (2Н,
(C–O), 600 (C–I)
Н4, J1 4.0, J2 1.2), 6.28 d.t (1Н, Н3, J1 4.0, J2 1.2)
3350–3500 (OH), 1625 (HC=CI), 1100, (DMSO-d6–CCl4, 1 : 3): 1.27 d (3Н, Н5, J 6.5), 2.93 br.s (2Н, С1ОН, С4ОН),
1Н NMR spectrum
IIа + IIIa
IIb + IIIb
IIc + IIIc
IId + IIId
1050 (C–O), 960 (CH=), 600 (C–I)
3.52 d [2Н, Н1, J 7, (IIb)], 3.78 q [1Н, Н4, J 6.5, (IIIb)], 3.90 s [2Н, Н1,
(IIIb)], 4.20–4.35 m [1Н, Н4, J 6.5, (IIb)], 5.95 d.t [1Н, Н2, J1 7, J2 1.2,
(IIIb)], 6.13 t [1Н, Н3, J 6.5, (IIb)]
3350–3400 (OH), 1625 (HC=CI), 1100, (СDCl3): 1.22 t (3Н, Н6, J 6.0), 1.40–1.80 m (2Н, Н5), 4.15 d [2Н, Н1, J 8.3,
1050 (C–O), 960 (CH=), 600 (C–I)
(IIc)], 4.22 s [2Н, Н1, (IIIc)], 4.18–4.28 m (1Н, Н4), 4.42 br.s (2Н, С1ОН,
С4ОН), 5.98 d.t [1Н, Н3, J1 7.5, J2 1.5, (IIIc)], 6.22 t.d [1Н, Н2, J1 6.0, J2
1.0, (IIc)]
3300–3500 (OH), 1630 (HC=CI), 1100, (DMSO-d6): 0.90 t (3Н, Н7, J 6.8), 1.20–1.52 m (4Н, Н5, Н6), 3.62 t (2Н, Н4,
1020 (C–O), 960 (CH=), 600 (C–I)
J 7.1), 3.98–4.06 m [2Н, Н1, (IId)], 4.02 s [2Н, Н1, (IIId)], 4.50 d [1Н,
С4ОН, J 7.1, (IIId)], 4.56 t [1Н, С1ОН, J 7.2, (IId)], 4.92 d [1Н, С4ОН,
J 7.2, (IId)], 5.22 t [1Н, С1ОН, J 7.1, (IIId)], 5.91 d [1Н, Н3, J 7.2, (IIId)],
6.09 t [1Н, Н2, J 7.1, (IId)]
3300–3500 (OH), 3040, 1560, 1510, 740, (DMSO-d6–CCl4, 1 : 3): 4.15 d (2Н, Н4, J 7.0), 4.89 t (1Н, Н2, J 7.0), 5.09 t
690 (monosubstituted benzene ring), 1630 (1Н, С4ОН, J 7.0), 5.33 d (1Н, Н1, J 7.0), 5.66 d (1Н, С1ОН, J 7.0), 7.20–
IIe
IIf
(HC=CI), 1100 (C–O), 860 (CH=), 600
(C–I)
7.35 m (5Н, С6Н5)
3300–3500 (OH), 1640 (Z-HC=CI), 1630 (СDCl3): 0.90 t (6Н, Н1, Н8, J 7.0), 1.40–1.60 m (4Н, Н2, Н7), 3.56 br.s (2Н,
(Е-HC=CI), 1080, 1050 (C–O), 960
(Z-CH=), 850 (Е-CH=), 600 (C–I)
С3ОН, С6ОН), 3.63 q (1Н, Н6, J 7.0), 4.28 t (1Н, Н3, J 7.0), 5.92 d.d (1Н,
Н5, J1 7.5, J2 1.0, Z-isomer), 5.97 d.d (1Н, Н5, J1 7.5, J2 0.8, E-isomer)
IIg + IIIg
IVgа
3300–3500 (OH), 1625 (HC=CI), 1150
(C–O), 960 (CH=), 600 (C–I)
(DMSO-d6): 0.92 t (6Н, Н1, С2СН3, J 7.0), 1.15–1.60 m (4Н, Н6, Н7), 1.37 s
(3Н, Н8), 1.55–1.63 m [1Н, Н5, (IIg)], 4.14–4.20 m [1Н, Н5, (IIIg)], 4.78
br.s (2Н, С2ОН, С5ОН), 5.82 d [1Н, Н4, J 7.0, (IIg)], 6.18 s [1H, Н3, (IIIg)]
3300–3500 (OH), 1950 (C=C=С), 1020– (DMSO-d6): 0.88 t (3Н, Н1, J 6.9), 1.32–1.62 m (4Н, Н2, Н3), 1.57–1.65 m
1000 (C–O), 840 (C=C=СН)
(6Н, Н8, С7СН3), 3.10 br.s (1Н, ОН), 4.45–4.53 m (1Н, Н4), 5.58–5.65 m
(1Н, Н5)
IIhа
3300–3500 (OH), 1625 (HC=CI), 1150, (СDCl3): 0.88 t (3Н, Н6, J 7.0), 1.22 s (3Н, С4СН3), 1.55 and 1.78 q (2Н, Н5,
1020 (C–O), 960 (CH=), 600 (C–I)
J 7.0), 4.96 d (2Н, Н1, J 7.0), 5.10 br.s (2Н, С1ОН, С4ОН), 5.24 t (1Н, Н2, J
7.0)
IIIhа
3300–3500 (OH), 1620 (HC=CI), 1100, (DMSO-d6): 0.88 t (3Н, Н6, J 7.0), 1.30 s (3Н, С4СН3), 1.55 and 1.78 q (2Н,
1020, 1000 (C–O), 960 (CH=), 600 (C–I)
Н5, J 7.0), 4.0 br.s (1Н, С4ОН), 4.03 s (2Н, Н4), 5.28 t (1Н, С1ОН, J 7.0),
6.33 s (1Н, Н3)
IVhа
IIi
3300–3500 (OH), 1950 (C=C=C), 1200– (DMSO-d6): 0.88 t (3Н, Н6, J 7.0), 1.48–1.54 m (3Н, С4СН3), 1.97–2.06 m
1000 (C–O), 840 (C=C=CH)
(2Н, Н5), 3.93 br.s (1Н, ОН), 4.56 d (2Н, Н1, J 7.1), 5.75–5.80 m (1Н, Н2)
3300–3500 (OH), 1640 (Z-HC=CI), 1630 (DMSO-d6): 0.92 t (6Н, Н1, Н10, J 7.0), 1.20–1.44 m (8Н, Н2, Н3, Н8, Н9),
(Е-HC=CI), 1080, 1050 (C–O), 960
(Z-CH=), 850 (Е-CH=), 600 (C–I)
3.40–3.55 m (1H, Н7), 4.08–4.20 m (1Н, Н4), 4.41 d (1Н, С7ОН, J 6.0,
Z-isomer), 4.46 d (1Н, С7ОН, J 6.0, Е-isomer), 4.82 d (1Н, С4ОН, J 5.0, Z-
isomer), 4.93 d (1Н, С4ОН, J 5.0, Е-isomer), 5.82 d.d (1Н, Н6, J1 7.5, J2
1.0, Z-isomer), 5.88 d.d (1Н, Н6, J1 7.5, J2 0.8, Е-isomer)
3300–3500 (OH), 3040, 3020, 1590, 1510, (СDCl3): 0.98 t (3Н, Н6, J 7.0), 1.56–1.74 m (2Н, Н5), 2.20 br.s (2Н, С1ОН,
740, 700 (monosubstituted benzene ring), С4ОН), 4.36 d.t (1Н, Н4, J1 7.6, J2 6.4), 5.12 d (1Н, Н1, J 0.8), 6.21 d.d (1Н,
1625 (HC=CI), 1100, 1050 (C–O), 960 Н3, J1 7.7, J2 1.0), 7.15–7.45 m (5Н, С6Н5)
(CH=), 600 (C–I)
IIj
a Compounds were isolated by column chromatography.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 3 2014