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Organic & Biomolecular Chemistry
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ARTICLE
Journal Name
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Colorless oil, 2.91 g, yield 88%, Rf = 0.62 (PE/EA = 10:1, v/v). H NMR ppm) = 138.5, 128.8, 128.2, 126.1, 75.3, 72.0, 36.2, 32.0, 23.6. GC-
DOI: 10.1039/C6OB02387H
(CDCl3, 400 MHz) (δ, ppm) = 7.29 (t, J = 7.9 Hz, 2H, ArH), 6.97 (t, J = MS (EI) m/z = 194 (M)+ for C11H14OS.
7.6 Hz, 1H, ArH), 6.91 (d, J = 8.4 Hz, 2H, ArH), 4.22 (dd, J = 10.2, 5.4
Benzyloxymethylthiirane (2g)
Hz, 1H in CH2O), 3.90 (dd, J = 10.2, 7.2 Hz, 1H in CH2O), 3.303.24
(m, 1H, CHS), 2.61 (d, J = 6.0, Hz, 1H in CH2S), 2.33 (d, J = 5.2, Hz, 1H
in CH2S). 13C NMR (101 MHz, CDCl3) (δ, ppm) = 158.4, 129.5, 121.2,
114.7, 72.5, 31.4, 24.0. GC-MS (EI) m/z = 166 (M)+ for C9H10OS.
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Colorless oil, 2.56 g, yield 68%, Rf = 0.39 (PE/EA = 10:1, v/v). H NMR
(CDCl3, 400 MHz) (δ, ppm) = 7.35-7.26 (m, 5H, ArH), 4.60 (d, J = 10.8
Hz, 1H in ArCH2), 4.56 (d, J = 10.8 Hz, 1H in ArCH2), 3.68 (dd, J = 10.4,
5.6 Hz, 1H, OCHHCH), 3.48 (dd, J = 10.4, 6.8 Hz, 1H, OCHHCH), 3.13-
3.07 (m, 1H, SCH), 2.51 (d, J = 6.0 Hz, 1H in SCH2), 2.20 (dd, J = 5.2,
(4-Methylphenoxy)methylthiirane (2b)
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Colorless oil, 2.00 g, yield 56%, Rf = 0.91 (PE/EA = 5:1, v/v). H NMR 1.2 Hz, 1H in SCH2). 13C NMR (101 MHz, CDCl3) (δ, ppm) = 137.8,
(CDCl3, 400 MHz) (δ, ppm) = 7.07 (d, J = 8.4 Hz, 2H, ArH), 6.80 (d, J = 128.4, 127.8, 127.7, 74.6, 73.1, 32.1, 23.8. GC-MS (EI) m/z = 180
8.4 Hz, 2H, ArH), 4.18 (dd, J = 10.2, 5.6 Hz, 1H in CH2O), 3.85 (dd, J = (M)+ for C11H12OS.
10.2, 7.2 Hz, 1H in CH2O), 3.273.21 (m, 1H, CHS), 2.58 (d, J = 6.4 Hz,
1H in CH2S), 2.312.78 (m, 4H, 1H in CH2O & CH3). 13C NMR (101
(4-Chlorophenylthio)methylthiirane (2h)
MHz, CDCl3) (δ, ppm) = 156.3, 130.5, 129.9, 114.6, 72.8, 31.4, 24.0,
20.4. GC-MS (EI) m/z = 180 (M)+ for C10H12OS.
Colorless oil, 780 mg, yield 15%, Rf = 0.77 (PE/EA = 10:1, v/v). IR
(KBr): v = 2921, 2849, 1643, 1573, 816 cm-1. 1H NMR (CDCl3, 400
MHz) (δ, ppm) = 7.29 (t, J = 2.8 Hz, 1H, ArH), 7.27 (t, J = 2.4 Hz, 1H,
ArH), 7.21 (t, J = 2.8 Hz, 1H, ArH), 7.18 (t, J = 2.0 Hz, 1H, ArH), 3.30
(3-Methylphenoxy)methylthiirane (2c)
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Colorless oil, 1.79 g, yield 50%, Rf = 0.62 (PE/EA = 10:1, v/v). H NMR (dd, J = 13.6, 5.2 Hz, 1H in ArSCH2), 2.99 (ddt, J = 10.0, 8.4, 5.2 Hz,
(CDCl3, 400 MHz) (δ, ppm) = 7.08 (t, J = 7.6 Hz, 1H, ArH), 6.70 (d, J = 1H, SCH), 2.73 (dd, J = 13.6, 8.4 Hz, 1H in ArSCH2), 2.40 (d, J = 5.2 Hz,
7.6 Hz, 1H, ArH), 6.656.61 (m, 2H, ArH), 4.11 (dd, J = 10.4, 5.6 Hz, 1H in SCH2), 2.02 (dd, J = 5.2, 1.2 Hz, 1H in SCH2). 13C NMR (101 MHz,
1H in CH2O), 3.79 (dd, J = 10.4, 7.2 Hz, 1H in CH2O), 3.203.14 (m, CDCl3) (δ, ppm) = 133.5, 133.1, 132.3, 129.2, 41.3, 33.3, 25.9. GC-
1H, CHS), 2.51 (d, J = 6.4 Hz, 1H in CH2S), 2.24 (s, 3H, CH3), 2.23 (d, J MS (EI) m/z = 216 (M)+ for C9H9ClS2.
= 5.6 Hz, 1H in CH2S). 13C NMR (101 MHz, CDCl3) (δ, ppm) = 158.4,
Benzylthiirane (2i)
139.5, 129.2, 122.0, 115.5, 111.5, 72.4, 31.4, 23.9, 21.5. GC-MS (EI)
m/z = 180 (M)+ for C10H12OS.
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Colorless oil, 600 mg, yield 44%, Rf = 0.30 (PE/DCM = 10:1, v/v). H
NMR (CDCl3, 400 MHz) (δ, ppm) = 7.347.23 (m, 5H, ArH), 3.123.06
(m, 1H, CHS), 2.96 (dd, J = 14.4, 6.0 Hz, 1H in ArCH2), 2.92 (dd, J =
(4-Methoxyphenoxy)methylthiirane (2d)
White solid, 6566 oC, 2.35 g, yield 60%, Rf = 0.75 (PE/EA = 3:1, v/v). 14.4, 7.2 Hz, 1H in ArCH2), 2.55 (d, J = 5.8 Hz, 1H in CH2S), 2.28 (d, J
1H NMR (CDCl3, 400 MHz) (δ, ppm) = 6.896.82 (m, 4H, ArH), 4.16 = 5.8 Hz, 1H in CH2S). 13C NMR (101 MHz, CDCl3) (δ, ppm) = 139.2,
(dd, J = 10.4, 5.6 Hz, 1H in CH2O), 3.86 (dd, J = 10.0, 6.8 Hz, 1H in 128.6, 128.5, 126.6, 42.6, 35.7, 25.6. GC-MS (EI) m/z = 150 (M)+ for
CH2O), 3.77 (s, 3H, CH3), 3.24 (dt, J = 6.8, 5.5 Hz, 1H, SCH), 2.59 (d, J C9H10S.
= 6.0 Hz, 1H in SCH2), 2.30 (dd, J = 5.2, 1.2 Hz, 1H in SCH2). 13C NMR
n-Hexylthiirane (2j)
(101 MHz, CDCl3) (δ, ppm) = 154.2, 152.5, 115.8, 114.6, 73.4, 55.6,
31.5, 23.9. GC-MS (EI) m/z = 196 (M)+ for C10H12O2S.
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Colorless oil, 1.10 g, yield 38%, Rf = 0.85 (PE/EA = 10:1, v/v). H NMR
(CDCl3, 400 MHz) (δ, ppm) = 2.91-2.84 (m, 1H, SCH), 2.49 (d, J = 6.0
Hz, 1H in SCH2), 2.14 (dd, J = 6.0, 0.8 Hz, 1H in SCH2), 1.86-1.78 (m,
(4-Chlorophenoxy)methylthiirane (2e)
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Colorless oil, 1.89 g, yield 47%, Rf = 0.56 (PE/EA = 10:1, v/v). H NMR 1H, SCHCHH), 1.53-1.45 (m, 5H, 1H in CH2, & 2CH2), 1.45-1.23 (m,
(CDCl3, 400 MHz) (δ, ppm) = 7.15 (d, J = 8.4 Hz, 2H, ArH), 6.77 (d, J = 4H, 2CH2), 0.89 (t, J = 6.4 Hz, 3H, CH3). 13C NMR (101 MHz, CDCl3) (δ,
8.4 Hz, 2H, ArH), 4.13 (dd, J = 10.8, 2.0 Hz, 1H in CH2O), 3.82 (dd, J = ppm) = 36.6, 36.0, 31.7, 29.3, 28.9, 25.9, 22.5, 14.0. GC-MS (EI) m/z
10.8, 5.6 Hz, 1H in CH2O), 3.283.24 (m, 1H, CHS), 2.82 (t, J = 4.4 Hz, = 144 (M)+ for C8H16S.
1H in CH2S), 2.672.66 (m, 1H in CH2S). 13C NMR (101 MHz, CDCl3)
2-Methyl-2-[(4-methylphenoxy)methyl]thiirane (2k)
(δ, ppm) = 157.0, 129.3, 126.1, 115.9, 69.0, 50.0, 44.5. GC-MS (EI)
m/z = 200 (M)+ for C9H9ClOS.
Colorless oil, 534 mg from 4k (1.00 g, 5.61 mmol), yield 49%, Rf =
0.84 (PE/EA = 10:1, v/v). IR (KBr): v = 3030, 2983, 2923, 1613, 1585,
1458, 817 cm-1. 1H NMR (CDCl3, 400 MHz) (δ, ppm) = 7.08 (d, J = 8.0
(2-Phenylethyl)oxymethylthiirane (2f)
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Colorless oil, 1.30 g, yield 29%, Rf = 0.38 (PE/EA = 20:1, v/v). H NMR Hz, 2H, ArH), 6.82 (d, J = 8.0 Hz, 2H, ArH), 4.14 (d, J = 9.6 Hz, 1H in
(CDCl3, 400 MHz) (δ, ppm) = 7.28 (t, J = 7.6 Hz, 2H, ArH), 7.227.17 OCH2), 3.86 (d, J = 9.6 Hz, 1H in OCH2), 2.52 (s, 1H in SCH2), 2.47 (s,
(m, 3H, ArH), 3.70 (t, J = 7.2 Hz, 2H, CH2O), 3.63 (dd, J = 10.8, 5.6 Hz, 1H in SCH2), 2.29 (s, 3H, ArCH3), 1.75 (s, 3H, SCCH3). 13C NMR (101
1H in OCH2), 3.43 (dd, J = 10.8, 6.8 Hz, 1H in OCH2), 3.063.00 (m, MHz, CDCl3) (δ, ppm) = 156.6, 130.4, 129.9, 114.6, 76.3, 42.5, 32.7,
1H, SCH), 2.89 (t, J = 7.2 Hz, 2H, ArCH2), 2.47 (d, J = 6.0 Hz, 1H in 23.5, 20.5. GC-MS (EI) m/z = 194 (M)+ for C11H14OS.
SCH2), 2.16 (d, J = 5.2Hz, 1H in SCH2). 13C NMR (101 MHz, CDCl3) (δ,
2-Methyl-2-[(3-methylphenoxy)methyl]thiirane (2l)
6 | J. Name., 2012, 00, 1-3
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