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Volumn 78, Issue 2, 2009, Pages 325-330

Effect of a metal salt on thiiranation of 2 ́-adamantylidene-9-benzonorbornenylidene with 4,4 ́-dithiodimorpholine and acetic anhydride

Author keywords

4,4 dithiodimorpholine; Acetic Anhydride; Lithium Perchiorate; Thiiranation; Thiirane

Indexed keywords

EID: 62649168387 PISSN: 03855414 EISSN: None Source Type: Journal
DOI: 10.3987/COM-08-11550 Document Type: Article

Times cited : (3)

References (17)

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14
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- Typical procedures for thiiranaton of 1 with 4 and Ac20 in a metal-salt solution: To a Et20 solution of a metal salt (3.0 mL) was added 1 (20.l mg, 73 μmol) and 4 (17.2 mg, 73 μmol, After the mixture was cooled to -15 °C, Ac20 (6.8 μL, 73 μmol) was added dropwise to the mixture. After stirring for 45 h at the same temperature, the reaction was quenched by the addition of ice water. After the mixture was diluted with Et20, the organic layer was separated, washed with H2O three times, dried over MgS04, and evaporated under reduced pressure. The residue was chromatographed on a column of silica gel and the column was eluted with hexane to give a mixture of 1, 2, and 3, and with CH2Cl2/hexane (l:5) to give a mixture of oxiranes 5 and 6. The product ratios were estimated by 1H NMR
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15
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16
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- 5: colorless crystals (from CH2Cl2/MeOH, mp 202.5-203.0 °C; 1H NMR (300.1 MHz) δ 1.01-1.11 (m, 2H, 1.28-1.37 (m, 2H, 1.52-l.73 (m, 9H, 1.85-1.92 (m, 1H, 1.93-2.04 (m, 2H, 2.95-3.03 (m, 2H, 7.10-7.22 (m, 4H, 13C NMR (50.3 MHz) δ25.2, 26.8, 27.1, 34.48, 34.54, 36.5, 36.8, 42.9, 72.1, 86.8, 120.8, 126.9, 144.9; IR (KBr) 3055, 2995, 2976, 2932, 2909, 2846, 1504, 1460, 1446, 1351, 1280, 1238, 1143, 1102, 1066, 1003, 958, 938, 927, 881, 851, 836, 769, 752, 686, 641, 613 cm-1; Anal. Calcd for C21H24N2O: C, 86.25; H, 8.27. Found: C, 86.22; H, 8.35. 6: colorless crystals (from CH2Cl2/MeOH, mp 198.0-198.5 °C; 1H NMR (300.1 MHz) δ 1.29-1.37 (m, 2H, 1.67-2.06 (m, 14H, 2.11-2.21 (m, 2H, 3.05-3.12 (m, 2H, 7.09-7.17 (m, 2H, 7.18-7.26 (m, 2H, 13C NMR (50.3 MHz) δ 25.2, 27.0, 27.3, 33.6, 34.8, 36.7, 37.5, 43.7, 79.2, 79.4, 121
- 20: C, 86.25; H, 8.27. Found: C, 86.01; H, 8.31.

17
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- Wiley-Interscience, New York
- Cotton F.A., Wilkinson G., Murillo C.A., and Bochmami M. Advanced Inorganic Chemistry. 6th ed. (1999), Wiley-Interscience, New York 568-569
- (1999) Advanced Inorganic Chemistry. 6th ed. , pp. 568-569
- Cotton, F.A.¹ Wilkinson, G.² Murillo, C.A.³ Bochmami, M.⁴

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