960
C. Santi et al.
MeCN (3 mL) and water (1 mL) 1 mmol of olefin 1 was added. The re-
action was stirred at reflux for 12–24 h. The crude product was purified
by flash chromatography on a silica gel column using a mixture of di-
ethyl ether-dichloromethane (99:1) as eluant. All the compounds were
fully characterized by 1H-NMR, 13C-NMR experiments and by GC-MS
analysis. Selected physical and spectral data are reported below.
(1S, 2S)-1-Phenyl-1,2-dihydroxycyclohexane7
C12H16O2, Oil [α]2D0.8 = −12.8 (c=0.52, CHCl3) IR (HATAR): ν(2OH) =
3504.99 cm−1; 1H NMR δ 7.55–7.50 ppm (m, 2H, 2CHAr), 7.40–7.35 (m,
3
3
2H, 2CHAr), 7.30–7.25 (m, 1H, CHAr), 3.99 (dd, 1H, J=4.5 Hz, J =
11.0 Hz, CHOH), 2.70–2.60 (br, s, OH), 1.90–1.80 (m, 3H), 1.80–1.60
(m, 4H), 1.60–1.50 (m, 1H), 1.45–1.40 (m, 1H); 13C NMR δ 146.3, 128.4,
126.9, 125.1, 75.7, 74.5, 38.5 29.2, 24.3, 21.0; GC-MS (70 eV): m/z (%):
192 (73) [M+.], 174 (31), 145 (16), 133 (100), 120 (50), 105 (66), 91 (22),
77 (39), 70 (13), 55 (24).
REFERENCES AND NOTES
[1] (a) M. Tiecco, L. Testaferri, C. Santi, C. Tomassini, F. Marini, L. Bagnoli, and A.
Temperini, Chem. Eur. J., 8, 1118 (2002); (b) M. Tiecco, L. Testaferri, C. Santi, C.
Tomassini, F. Marini, L. Bagnoli, and A. Temperini, Angew. Chem. Int. Ed., 42, 3131
(2003); (c) M. Tiecco, L. Testaferri, C. Santi, C. Tomassini, S. Santoro, F. Marini, L.
Bagnoli, A. Temperini, and F. Costantino Eur. J. Org. Chem. 4867 (2006); (d) M.
Tiecco, L. Testaferri, C. Santi, C. Tomassini, R. Bonini, F. Marini, L. Bagnoli, and
A. Temperini Org. Lett., 6, 4751 (2004).
[2] (a) M. Tiecco, In Electrophilic Selenium, Selenocyclizations, T. Wirth, Ed. (Springer-
Verlag, Heidelberg, 2000) p. 7; (b) Organoselenium Chemistry—A Pratical Approach,
T. G. Back, Ed. (Oxford, New York, 2000); (c) T. Wirth, Angew. Chem. Int. Ed., 39,
3742 (2000).
[3] (a) M. Tiecco, L. Testaferri, M. Tingoli, and F. Marini Synlett, 373 (1994), and refer-
ences cited therein; (b) M. Tiecco, L. Testaferri, M. Tingoli, L. Bagnoli, and C. Santi,
J. Chem. Soc. Chem. Commun., 637 (1993).
[4] (a) S. Fukuzawa, K. Takahashi, H. Kato, and H. Yamazaki, J. Org. Chem., 62, 7711
(1997); (b) T. Wirth, S.Hauptli, and M. Leuenberger Tetrahedron Asymmetry, 9, 547
(1998).
[5] M. Tiecco, L. Testaferri, M. Tingoli, and F. Marini, J. Org. Chem., 56, 5207 (1991),
and references cited therein.
[6] 1H and 13C NMR spectra were recorded at 400 and 100.62 MHz, respectively, on a
Bruker Avance-DRX 400 instrument. Unless otherwise specified, CDCl3 was used
as the solvent and TMS as internal standard. GC-MS analyses were carried out with
an HP-6890 gas chromatograph (dimethyl silicone column, 12.5 m) equipped with an
HP-5973 mass-selective detector. IR spectra were recorded on a JASCO FT/IR-410
spectrophotometer using a multiple reflection horizontal ATR (HATR) accessory.
Optical rotations were measured with a JASCO DIP-1000 digital polarimeter.
[7] S. Jonsson, H. Adolfsson, and J.-E. Backvall, Org. Lett., 3, 3463 (2001).