REFERENCES
- Oae , S. 1982 . Organic Chemistry of Sulfur Kyoto : Kagakudoujin . On the preparation and reaction of sulfonium salts, see
- Aggarwal , V. K. , Calamai , S. and Ford , J. G. 1997 . J. Chem. Soc. Perkin Trans. 1 , : 593 – 599 . For recent examples on the study of sulfonium salts, see, references cited therein. 2
- Paulmier , C. 1986 . “ Selenium Reagents and Intermediates in Organic Synthesis ” . In Organic Chemistry Series Edited by: Baldwin , J. E. Vol. 4 , Oxford : Pergamon Press .
- Li , A.-H. , Dai , L.-X and Aggarwal , V. K. 1997 . Chem. Rev. , 97 : 2341 – 2372 .
- Pope , W. J. and Neville , A. J. 1902 . Chem. Soc. , : 1552
- Kobayashi , M. , Koyabu , K. , Shimizu , T. , Umemura , K. and Matsuyama , H. 1986 . Chem. Lett. , : 2117
- Shimizu , T. and Kamigata , N. 1997 . Org. Prep. Proed. Int. , 29 : 605 – 629 .
- Takahashi , T. , Kurose , N. , Kawanami , S. , Nojiri , A. , Arai , Y. , Koizumi , T. and Shiro , M. 1995 . Chem. Lett. , : 379 – 380 .
- Zhang , J. , Saito , S. and Koizumi , T. 1997 . Tetrahedron: Asymmetry , 8 : 3357 – 3361 .
- Zhang , J. , Saito , S. and Koizumi , T. 1998 . J. Org. Chem. , 63 : 5423 – 5429 .
- General procedure for the synthesis of selenonium salts: To a solution of selenurane (0.1 mmol) in CH2Cl2(3 ml) was added a solution of RMgX (0.12 mmol, in THF or Et2 O) dropwise at −78°C under N2. The reaction mixture was stirred and allowed to warm up to 0°C during ca. 1 h. Then the mixture was stirred at 0°C for 2 h. The reaction mixture was worked up by addition of saturated aqueous NH4Cl solution (2 ml), followed by extraction with CH2Cl2(20 ml × 2). The combined organic layer was washed with H2O (4ml × 1) and brine (4 ml × 1), dried over MgSO4, and then concentrated to dryness. Purification of the residue by recrystallization from hexane and CH2Cl2afforded the product as a colorless crystal. Satisfactory analytical (combustion and high resolution mass) and spectral (IR, 1H NMR, Mass) data were obtained for all new isolable compounds. Selected data for compound 2b: mp 157–159°C; [α]26 D-37.00 (c, 0.71, CHCl3); IR (KBr) 2954, 1455, 1258 cm−1; 1H NMR (300 MHz, CDCl3) δ: 0.88 (s, 3H), 0.98 (t, 3H, J = 7.1), 1.1–1.24 (m, 2H), 1.14 (s, 3H), 1.52 (dt, 2H, J = 7.1, 7.7), 1.6–2.18 (m, 7H), 2.94 (s, 3H), 3.18 (d, 1H, J = 11.5), 3.42–3.61 (m, 3H), 4.0 (dd, 1H, J = 3.8, 6.6), 5.95 (d, 1H, J = 4.9); 13C NMR(75 MHz, CDCl3) δ: 13.9, 20.8, 20.9, 21.1, 22.9, 27.0, 27.5, 32.7, 41.0, 42.3, 43.2, 45.7, 49.0, 51.5, 75.8; Ms m/z: 290, 288, 270, 268, 257, 255, 229, 227, 215, 213, 135, 109, 93; Anal. Calcd for C15H29ClOSe: C, 53.02; H, 8.60. Found: C, 52.95; H, 8.84
- Crystallographic data for 2b: prismatic, space group, P21212 (#18) with a = 9.895(5)Å, b = 25.621(7)Å, c 6.724(7)Å, V = 1704.0(1)Å3, and Z = 4 (dcalcd = 1.324 g cm−3), μ (MoKα = 23.49cm−1 absorption corrected by ω scans; 1780 unique reflections; 985 with I > 3.00σ(I) were used in refinement; R = 4.3%, Rw = 4.4%. Selected bond lengths (Å) and angles (deg) are as follows: Se-C(1), 1.98(1); Se-C(2), 1.91(1); Se-C(3), 1.95(1); C(1)-Se-C(2), 99.7(5); C(1)-Se-C(3), 94.4(6); C(2)-Se- C(3), 95.6(6)