Solid state optical activity of dichalcogenides: Isolation by chiral crystallization and determination of absolute configuration

Organic Letters

Volumn 3, Issue 23, 2001, Pages 3639-3641

  Shimizu, Toshio ^a   Isono, Hiromi ^a   Yasui, Masanori ^b   Iwasaki, Fujiko ^b   Kamigata, Nobumasa ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

^b UNIVERSITY OF ELECTRO COMMUNICATIONS   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHALCONE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ARTICLE; CIRCULAR DICHROISM; CONFORMATION; CRYSTALLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CHALCONE; CIRCULAR DICHROISM; CRYSTALLIZATION; CRYSTALLOGRAPHY, X-RAY; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0035891789     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010172g     Document Type: Article

References (93)

1. Review: Steudel, R. Angew. Chem. 1975, 87, 683; Angew. Chem., Int. Ed. Engl. 1975, 14, 655.
2. Review: Steudel, R. Angew. Chem. 1975, 87, 683; Angew. Chem., Int. Ed. Engl. 1975, 14, 655.
3. Lee, J. D.; Bryant, M. W. R. Acta Crystallogr. 1969, B25, 2094.
4. Sacerdoti, M.; Gilli, G.; Domino, P. Acta Crystallogr. 1975, B31, 327.
5. For examples: (a) Kansikas, J.; Sipilä, K. Acta Crystallogr. 2000, C56, 72.
6. (b) Koritsanszky, T.; Buschmann, J.; Luger, P.; Schmidt, H.; Steudel, R. J. Phys. Chem. 1994, 98, 5416.
7. (c) Rindorf, G.; Jørgensen, F. S.; Snyder, J. P. J. Org. Chem. 1980, 45, 5343.
8. (d) Ladd, M. F. C.; Povey, D. C.; Yu, P.-Y.; Chan, T.-L.; Mak, T. C. W. Acta Crystallogr. 1978, B34, 2935.
9. (e) Lee, J. D.; Bryant, M. W. R. Acta Crystallogr. 1969, B25, 2497.
10. (f) Hordvik, A. Acta Chem. Scand. 1966, 20, 1885, and references therein.
11. Borghi, R.; Lunazzi, L.; Placucci, G.; Cerioni, G.; Foresti, E.; Plumitallo, A. J. Org. Chem. 1997, 62, 4924.
12. (a) Yokozeki, A.; Bauer, S. H. J. Phys. Chem. 1976, 80, 618.
13. (b) Winnewisser, G.; Winnewisser, M.; Gordy, W. J. Chem. Phys. 1968, 49, 3465.
14. Steudel, R.; Schmidt, H.; Baumeister, E.; Oberhammer, H.; Koritsanszky, T. J. Phys. Chem. 1995, 99, 8987.
15. Ostrowski, M.; Jeske, J.; Jones, P. G.; du Mont, W.-W. Chem. Ber. 1993, 126, 1355.
16. For examples: (a) Steudel, R.; Drozdova, Y.; Miaskiewicz, K.; Hertwig, R. H.; Koch, W. J. Am. Chem. Soc. 1997, 119, 1990.
17. (b) Shimizu, T.; Iwata, K.; Kamigata, N.; Ikuta, S. J. Chem. Res., Synop. 1997, 38; Miniprint 1997, 344.
18. (b) Shimizu, T.; Iwata, K.; Kamigata, N.; Ikuta, S. J. Chem. Res., Synop. 1997, 38; Miniprint 1997, 344.
19. (c) Bainbridgge, N.; Butler, A. R.; Görbitz, C. H. J. Chem. Soc., Perkin Trans. 2 1997, 351.
20. (d) Miaskiewicz, K.; Steudel, R. J. Chem. Soc. Dalton Trans. 1991, 2395.
21. (e) Dixon, D. A.; Zeroka, D.; Wendoloski, J. J.; Wasserman, Z. R. J. Phys. Chem. 1985, 89, 5334.
22. (f) Rauk, A. J. Am. Chem. Soc. 1984, 106, 6517.
23. (g) Jørgensen, F. S.; Snyder, J. P. Tetrahedron 1979, 35, 1399.
24. (h) Hinchcliffe, A. J. Mol. Struct. 1979, 55, 127.
25. (i) Snyder, J. P.; Carlsen, L. J. Am. Chem. Soc. 1977, 99, 2931.
26. (j) Allinger, N. L.; Hickey, M. J.; Kao, J. J. Am. Chem. Soc. 1976, 98, 2741.
27. (k) Allinger, N. L.; Kao, J., Chang, H.-M.; Boyd, D. B. Tetrahedron 1976, 32, 2867.
28. (l) Dixon, R. N., Hugo, J. M. V. Mol. Phys. 1975, 29, 953.
29. (m) Van Wart, M. E.; Shipman, L. L.: Scheraga. H. A. J. Phys. Chem. 1974, 79, 1848.
30. (n) Boyd, D. B. J. Phys. Chem. 1974, 78, 1554.
31. (o) Webb, J.; Strickland, R. W.; Richardson, F. S. J. Am. Chem. Soc. 1973, 95, 4775.
32. (p) Boyd, D. B. J. Am. Chem. Soc. 1972, 94, 8799.
33. (q) Linderberg, J.; Michl, J. J. Am. Chem. Soc. 1970, 92, 2619.
34. (r) Veillard, A.; Demuynck, J. Chem. Phys. Lett. 1970, 4, 476.
35. (s) Hillier, I. H.; Saunders, V. R.; Wyatt, J. F. Trans. Faraday Soc. 1970, 66, 2665.
36. (t) Schwartz, M. E. J. Chem. Phys. 1969, 51, 4182.
37. (u) Bergson, G. Arkiv. Kemi. 1962, 18, 409.
38. (v) Bergson, G. J. Arkiv. Kemi. 1958, 12, 233.
39. (a) Block, R.; Jansen, L. J. Chem. Phys. 1985, 82, 3322.
40. (b) Ewig, C. S.; Mei, E. H.; Van Wazer, J. R. Mol. Phys. 1980, 40, 241.
41. Cerioni, G.; Cremonini, M. A.; Lunazzi, L.; Placucci, G.; Plumitallo, A. J. Org. Chem. 1998, 63, 3933.
42. Kessler, H.; Rundel, W. Chem. Ber. 1968, 101, 3350.
43. (a) Pinto, R. M.; Leung, R. Y. N.; Sharma, R. D. Magn. Reson. Chem. 1988, 26, 729.
44. (b) Anderson, J. E.; Henriksen, L. J. Chem. Soc., Chem. Commun. 1985, 1397.
45. (c) Bushweller, C. H. Int. J. Sulfur Chem. 1973, 8, 103.
46. (d) Fraser R. R.; Boussard, G.; Saunders, J. K.; Lambert, J. B.; Mixan, C. E. J. Am. Chem. Soc. 1971, 93, 3822.
47. (e) Seel, F.; Gombler, W.; Budennz, R. Liebigs Ann. Chem. 1970, 725, 1.
48. (f) Thompson, Q. E.; Crutchfield, M. M.; Dietrich, M. W.; Pierron, E. J. Org. Chem. 1965, 30, 2692.
49. (g) Claeson, G.; Androes, G.; Calvin, M. J. Am. Chem. Soc. 1961, 83, 4357.
50. Marsh, R. E. Acta Crystallogr. 1952, 5, 458.
51. For examples: (a) Jeske, J.; Salzen, A. M.; de Mont, W. W.; Jones, P. G. Acta Crystallogr. 1998, C54, 1873.
52. (b) Ellison, J. J.; Ruhlandt-Senge, K.; Hope, H. H.; Power, P. P. Inorg. Chem. 1995, 34, 49.
53. (c) du Mont, W.-W.; Martens, A.; Pohl, S.; Saak, W. Inorg. Chem. 1990, 29, 4847.
54. (d) Morris, G. D.; Einstein, F. W. B. Acta. Crystallogr. 1986, C42, 1433.
55. (e) Van den Bossche, G.; Spirlet, M. R.; Dideberg, O.; Dupont, L. Acta Crystallogr. 1984, C40, 1979.
56. (f) Back, T. G.; Codding, P. W. Can. J. Chem. 1983, 61, 2749.
57. (g) Woodard, C. M,; Brown, D. S; Lee, J. D.; Massey, A. G. J. Organomet. Chem. 1976, 121, 333.
58. Kruse, F. M.; Marsh, R. E., McCullough, J. D. Acta Crystallogr. 1957, 10, 201.
59. D'Antonio, P.; George, C.; Lowrey, A. H.; Karle, J. J. Chem. Phys. 1971, 5 5, 1071.
60. Llabres, P. G., Dideberg, O.; Dupont, L. Acta Crystallogr. 1972, B28, 2438.
61. For examples: (a) Dukat, W.; Gall, F.; Meyer, C.; Mootz, D.; Naumann, D.; Nowicki, G.; Schulz, K. Z. Anorg. Allg. Chem. 1996, 622, 617.
62. (b) Lang, E. S.; Maichle-Mössmer, C.; Strähle, J. Z. Anorg. Allg. Chem. 1994, 620, 1678.
63. (c) Ludlow, S.; McCarthy, A. E. J. Organomet. Chem. 1981, 219, 169.
64. (d) Spirlet, M. R.; Van den Bossche, G.; Dideberg, O.; Dupont, L. Acta Crystallogr. 1979, 5, 102.
65. Wolfe, S. Acc. Chem. Res. 1972, 5, 102.
66. (a) Burdon, J.; Hotchkiss, J. C.; Jennings, W. B. J. Chem. Soc., Perkins Trans. 2 1976, 1052.
67. (b) Raban, M.; Noyd, D. A.; Bermann, L. J. Org. Chem. 1975, 40, 752.
68. While the term "chiral dichalcogenide" has sometimes been used, the chiralities of most of those compounds have been due to the substituents on the chalcogen atoms, see: (a) Wirth, T. Tetrahedron 1999, 55, 1.
69. (b) Nishibayashi, Y.; Uemura, S. Rev. Heteroatom Chem. 1996, 14, 83.
70. (a) Neubert, L. A.; Carmack, M. J. Am. Chem. Soc. 1974, 96, 943.
71. (b) Nagarajan, R.; Woody, R. W. J. Am. Chem. Soc. 1973, 95, 7212.
72. (c) Carmack, M.; Neubert, L. A. J. Am. Chem. Soc. 1967, 89, 7134.
73. (d) Fridrichsons, J.; Mathieson, A. M. Acta Crystallogr. 1967, 23, 439.
74. (e) Beecham, A. F.; Mathieson, A. M. Tetrahedron Lett. 1966, 3139.
75. (f) Beecham, A. F.; Fridrichsons, J.; Mathieson, A. M. Tetrahedron Lett. 1966, 3131.
76. (g) Djerassi, C.; Wolf, H.; Bunnenberg, E. J. Am. Chem. Soc. 1962, 84, 4552.
77. (h) Djerassi, C.; Fredga, A.; Sjöberg, B. Acta Chem. Scand. 1961, 15, 417.
78. (a) Casey, J. P.; Martin, R. B. J. Am. Chem. Soc. 1972, 94, 6141.
79. (b) Coleman, D. L.; Blout, E. R. J. Am. Chem. Soc. 1968, 90, 2405.
80. (c) Beychok, S.; Breslow, E. J. Biol. Chem. 1968, 243, 151.
81. (d) Beychok, S. Science 1966, 154, 1288.
82. Review: Snatzke, G. In The Chemistry of Organic Selenium and Tellurium Compounds. Vol. 1; Patai, S., Rappoport, Z., Ed.; John Wiley & Sons: New York, 1986; Chapter 17.
83. (a) Ringdahl, B.; Craig, J. C.; Zdansky, G.; Fredga, A. Acta Chem. Scand. 1980, B34, 735.
84. (b) Foss, O.; Johnsen, K.; Reistad, T. Acta Chem. Scand. 1964, 18, 2234.
85. (a) Armarego, W. L. F.; Turner, E. E. J. Chem. Soc. 1957, 13.
86. (b) Kuroda, R.; Mason, S. F. Tetrahedron 1981, 37, 1995.
87. Egartner, L.; Halla, F.; Schacherl, R. Z. Phys. Chem. B 1932, 18, 189.
88. Typical procedure for chiral crystallization of diphenyl dichalcogenides: ca. 1.0 g of diphenyl disulfide or diphenyl diselenide, which was preliminary purified by silica gel column chromatography and then recrystallization. was dissolved in refluxing ethanol (ca. 15 or 40 mL, respectively), and the solution was cooled slowly to room temperature. Precipitated crystals were collected by suction filtration to give chiral crystals of the disulfide (32-74%) or diselenide (16-73%). Similarly, 0.6 g of diphenyl ditelluride was recrystallized from hot petroleum ether (ca. 45 mL) to yield chiral crystals of the ditelluride (57-84%).
89. A mixture of a single crystal (ca. 2 ing) of the dichalcogenide and 100 mg of KBr was ground and formed into disk with a radius of 6.5 mm.
90. Theoretical study: Geometries, vibrational frequencies, and energies were calculated by using Density Functional Theory (B3LYP). The double-ζ plus polarization basis set of hydrogen, carbon, and sulfur atoms was used. The (5s 4p 2d/12s 8p 5d) and (10s 8p 4d/16s 11p 6d) basis sets were also used for the selenium and tellurium atoms, respectively.
91. (a) Djerassi, C.; Wolf, H.; Bunnenberg, E. J. Am. Chem. Soc. 1962, 84, 4552.
92. (b) Djerassi, C.; Fredga, A.; Sjöberg, B. Acta Chem. Scand. 1961, 15, 417.
93. -3. Absolute structure parameter was -0.02(5) for the P-form and 1.02(6) for the M-form.