Thiiranes from Oxiranes in the Presence of b-Cyclodextrin in Water
COMMUNICATIONS
1972, 627; c) B. Tamami, A. R. Kiasat, Synth. Commun.
1996, 26, 3953; d) N. Iranpoor, F. Kazemi, Synthesis 1996,
821; e) M. O. Brimeyer, A. Mehrota, S. Quici, A. Nigam,
S. L. Regen, J. Org.Chem. 1980, 45, 4254.
Experimental Section
General Information
1H NMR spectra were recorded on Gemini-200 MHz spec-
trometer in CDCl3, with TMS as internal standard. Mass
spectra were recorded on a Finnigan MAT 1020 mass
spectrometer operating at 70 eV. IR spectra were recorded
on Nicolet FT-IR spectrometer. Melting points were recorded
on B¸chi R-535 apparatus and are uncorrected. CH analyses
were recorded on a Vario EL analyser.
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General Procedure
b-Cyclodextrin (1 mmol) was dissolved in water (25 mL) at
608C, and the epoxide (1 mmol) dissolved in acetone (2 mL)
was added slowly with stirring. The mixture was cooled to room
temperature, potassium thiocyanate(1.5 mmol) was added and
the reaction was stirred at that temperature (Table 1). The
reaction mixture was extracted with ethyl acetate, filtered and
washed with brine. The organic phase was dried (Na2SO4),
filtered and the solvent was removed under vacuum. The crude
product was purified by silica gel column chromatography with
ethyl acetate:n-hexane (5:95) as eluent.
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and Practice, Oxford University Press, Oxford, 1998;
b) Green Chemistry, Frontiers in Benign Chemical Syn-
thesis and Processes, (Eds.: P. T. Anastas, T. C. William-
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Int. Ed. 2002, 41, 414.
Spectroscopic Data of New Compounds
2-[4-(2-Methoxyethyl)phenoxymethyl]thiirane (Table 1, en-
try 5): Colorless oil; IR (neat): n 2923, 1600, 1507, 1246,
1107 cmÀ1; 1H NMR (CDCl3, 400 MHz): d 2.25 (m, 1H), 2.50
(m, 1H), 2.75 (t, 2H, J 5.8 Hz), 3.12 (m, 1H), 3.25 (s, 3H), 3.38
(t, 2H, J 5.8 Hz), 3.72 (m, 1H), 4.20 (m, 1H), 6.71 (d, 2H, J
7.9 Hz), 7.05 (d, 2H, J 7.9 Hz); MS (EI): m/z 224; anal.
calcd. for C12H16O2S: C 64.25, H 7.19, S 14.29; found: C 64.29, H
7.22, S 14.31.
1-[4-(2-Thiiranylmethoxy)phenyl]-1-ethanone
(Table 1,
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[13] a) K. Surendra, N. S. Krishnaveni, Y. V. D. Nageswar,
K. R. Rao, J. Org. Chem. 2003, 68, 4994; b) K. Surendra,
N. S. Krishnaveni, M. A. Reddy, Y. V. D. Nageswar, K. R.
Rao, J. Org. Chem. 2003, 68, 2058; c) N. S. Krishnaveni,
K. Surendra, M. A. Reddy, Y. V. D. Nageswar, K. R.
Rao, J. Org. Chem. 2003, 68, 2018; d) M. A. Reddy, K.;
Surendra, N. Bhanumathi, K. R. Rao, Tetrahedron 2002,
58, 6003; e) M. A. Reddy, N. Bhanumathi, K. R. Rao,
Tetrahedron Lett. 2002, 43, 3237.
entry 6): Colorless oil; IR (neat): n 2924, 1691, 1584, 1245,
1153, 838 cmÀ1; 1H NMR (CDCl3, 400 MHz): d 2.20 (m, 1H),
2.50 (s, 3 H), 2.59 (m, 1H), 3.18 (m, 1H), 3.82 (m, 1H), 4.20 (m,
1H), 6.89 (d, 2H, J 8.0 Hz), 7.89 (d, 2H, J 8.0 Hz); MS (EI):
m/z 208; anal. calcd. for C11H12O2S: C 63.44, H 5.81, S 15.39;
found: C 63.48, H 5.84, S 15.41.
Acknowledgements
[14] M. O. Brimeyer, A. Mehrota, S. Quici, A. Nigam, S. L.
Regen, J. Org. Chem. 1980, 45, 4254.
We thank CSIR, New Delhi, India, for fellowships to KS and
MSR.
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istry, Pergamon, Oxford, 1996, 3, 253.
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Commun. 1970, 2.
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