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2. Typical procedure for solvent-free transformations of
alcohols with iodine
Alcohol 5f (solid) (1 mmol) and 5% of iodine
(0.05 mmol, 12.7 mg) were triturated in a glass mortar
for 1 min, transferred to a 15 ml flask and heated at
70 °C for 3 h. An aqueous solution of Na2S2O3Æ5H2O
(10%, 20 ml) was then poured into the cooled mixture
and the crude product was extracted with tert-butyl-
methyl-ether (35 ml) and washed with water. Pure
1,1,3-trimethyl-3-phenyl-indane (8, colourless oil) was
obtained by column chromatography (SiO2, hexane:
CH2Cl2 4:1) in 91% yield.
1H NMR (CDCl3): dH 1.03 (s, 3H), 1.34 (s, 3H), 1.69 (s,
3H), 2.19 (d, J = 13.0 Hz, 1H), 2.50 (d, J = 13.0 Hz,
1H), 7.10–7.28 (m, 9H); 13C NMR (76 MHz; CDCl3):
dC 30.4, 30.6, 30.9, 42.8, 50.8, 59.5, 122.5, 125.0, 125.4,
126.6, 127.2, 127.9, 148.7, 151.0, 152.1; IR (NaCl,
cmÀ1): 3061, 3021, 2959, 2863, 1599, 1445, 1312, 1202,
1028. 757, 700; m/z (EI, 70 eV): 236 (45%, M+), 221
(100), 143 (35), 91 (32); HRMS (EI): Calcd. Mass for
C18H20: 236.1565, Found mass 236.1574; Elemental
analysis: Calcd. For C18H20: C 91.47; H 8.53. Found
C 91.73; H 8.41.
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In the case of liquid substrates, 1 mmol of alcohol and
5% of iodine were mixed together in a 15 ml flask for
1 min and then left for various times at 25 °C or heated
at 60–70 °C.
Supplementary data
Supplementary data associated with this article can be
ˇ
14. Zmitek, K.; Zupan, M.; Stavber, S.; Iskra, J. Org. Lett.
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References and notes
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Media; Wiley & Sons: New York, 1997; (b) Lubineau, A.;
´
Auge, J.; Queneau, Y. Synthesis 1994, 741–760; (c)