4834
D. P. G. Hamon, K. L. Tuck / Tetrahedron 56 (2000) 4829±4835
compound as a colourless liquid (63 mg, 55%), care was
taken to include all fractions containing the epoxide to
avoid enrichment by fractionation. Chiral shift analysis of
the epoxide (4 mg) with Eu(hfc)3 (3 mg) in CCl4 (0.5 mL)
and C6D6 (0.08 mL) gave similar separation of the epoxy
protons as obtained for the racemic compound. The enan-
tiomeric excess (94^3% e.e.) measured was unchanged
from the optically enriched tosylate sample employed
(94^3% e.e.).
reaction mixture re¯uxed for 6 h. Then CH2Cl2 (10 mL)
was added and the solution was washed with sat. NaHCO3
(10 mL), H2O (50 mL), dried, and solvent removed to give a
yellow solid which was puri®ed by ¯ash chromatography
(CH2Cl2/hexanes 20/80, v/v), to give, in a 53% yield, the
title compound as a clear oil (176 mg, 0.49 mmol). dH
(200 MHz):1.33±2.04 (m, 8H, methylene envelope), 2.93
(t, J7.3 Hz, 2H, H20), 3.49 (m, 1H, H1), 3.68 (m, 3H,
H2 and H10), 7.26 (m, 8H, Ar-H and Se±Ar-H), 7.62 (m,
2H, Se±Ar-H). dC (50 MHz):21.1, 25.2, 29.4, 30.3, 36.6,
49.4, 69.7, 78.4, 126.0, 126.9, 128.2, 128.8, 129.0, 130.7,
134.1, 139.2. nmax(CDCl3): 2800(s), 1600(s), 1570(m),
trans-2-(Phenylselenyl)cyclohexyl(20-phenylethyl) ether
(14). trans-2-(2-Phenylethoxy)-cyclohexan-1-ol. To a solu-
tion of sodium hydride, (oil removed with dry benzene,
159 mg, 6.60 mmol) in THF (6 mL) and HMPA (0.4 mL)
was added 2-phenylethanol (0.25 mL, 2.10 mmol). The
solution was re¯uxed and to this was added dropwise cyclo-
hexane oxide (0.2 mL, 1.98 mmol) and further re¯uxed
overnight. CH2Cl2 (10 mL) was added and the solution
washed with sat. NH4Cl (10 mL), the aqueous layer further
extracted with CH2Cl2 (2£10 mL), the organic phase was
dried and solvent removed. The crude product was puri®ed
by ¯ash chromatography (EtOAc/hexanes, 20/80, v/v) then
further by distillation (1208C/0.1 mm Hg) to give, as a clear
oil, trans-2-(2-phenylethoxy)-cyclohexan-1-ol (130 mg,
0.59 mmol, 29%). dH (200 MHz):1.09 (m, 4H, methylene),
1.69 (m, 2H, methylene), 1.9±2.1 (m, 2H, methylene), 2.52
(br s, 1H, OH), 2.90 (t, J7.0 Hz, 2H, H20), 3.05 (m, 1H, H1
or H2), 3.37 (m, 1H, H1 or H2), 3.57 (dt, J7.4 and 9.1 Hz,
1H, H10, diastereotopic), 3.95 (dt, J6.6 and 9.2 Hz, 1H,
H10, diastereotopic), 7.28 (m, 5H, Ar-H). dC (50 MHz):23.9,
24.2, 29.2, 31.9, 36.7, 69.5, 73.7, 84.1, 126.3, 128.4, 128.9,
139.0. nmax(CDCl3): 3550 (m), 3400 (w), 2900 (s), 1600(m),
1500(m), 1260(m) cm21. m/z(FAB): 221 (MH1,9%),
203(5), 121(3), 105(100).
1500(s), 1420(s), 1350(s), 1290(s), 1230(s), 1160(s) cm21
.
m/z(FAB): 360(MH1,20%), 256(15), 239(41), 105(100).
Analytical results were not obtained.
Acknowledgements
K.L.T. is grateful for the receipt of an Australian Post-
graduate Award. We thank Rebecca Kennedy for the
observations referred to in Ref. 21.
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