Reaction of 2,6-xylyl isoselenocyanate with organolithium compounds

Tetrahedron

Volumn 52, Issue 37, 1996, Pages 12165-12176

  Maeda, Hajime ^a   Kambe, Nobuaki ^a   Sonoda, Noboru ^a   Fujiwara, Shin Ichi ^b   Shin Ike, Tsutomu ^b  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA DENTAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSELENIUM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030576892     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00707-7     Document Type: Article

References (111)

1. 1. (a) Paquer, D. Bull. Soc. Chim. Fr. 1975, 1439-1449.
2. (b) Nakamura, K.; Ohno, A. Kagaku No Ryoiki 1978, 32, 74-84; Chem. Abstr. 1978, 89, 5533y.
3. (b) Nakamura, K.; Ohno, A. Kagaku No Ryoiki 1978, 32, 74-84; Chem. Abstr. 1978, 89, 5533y.
4. (c) Viola, H.; Hartenhauer, H.; Mayer, R. Z. Chem. 1988, 28, 269-277.
5. (d) Metzner, P. Synthesis 1992, 1185-1199.
6. (e) Guziec, F. S. Jr. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S. Eds.; John Wiley & Sons, Inc.: New York, 1987; Vol 2, pp. 215-273.
7. 2. (a) Beak, P.; Worley, J. W. J. Am. Chem. Soc. 1970, 92, 4142-4143.
8. (b) Beak, P.; Worley, J. W. J. Am. Chem. Soc. 1972, 94, 597-604.
9. (c) Dagonneau, M.; Vialle, J. Bull. Soc. Chim. Fr. 1972, 2067-2068.
10. (d) Dagonneau, M.; Paquer, D.; Vialle, J. Bull. Soc. Chim. Fr. 1973, 1699-1702.
11. (e) Metzner, P.; Vialle, J. Bull Soc. Chim. Fr. 1973, 1703-1707.
12. (f) Dagonneau, M.; Vialle, J. Tetrahedron Lett. 1973, 3017-3020.
13. (g) Dagonneau, M.; Metzner, P.; Vialle, J. Tetrahedron Lett. 1973, 3675-3678.
14. (h) Dagonneau, M.; Vialle, J. Tetrahedron 1974, 30, 415-418.
15. (i) Dagonneau, M.; Vialle, J. Tetrahedron 1974, 30, 3119-3126.
16. (j) Dagonneau, M. J. Organomet. Chem. 1974, 80, 1-5.
17. (k) Beak, P.; Yamamoto, J.; Upton, C. J. J. Org. Chem. 1975, 40, 3052-3062.
18. (l) Ohno, A.; Nakamura, K.; Uohama, M.; Oka, S. Chem. Lett. 1975, 983-984.
19. (m) Ohno, A.; Nakamura, K.; Uohama, M.; Oka, S.; Yamabe, T.; Nagata, S. Bull. Chem. Soc. Jpn. 1975, 48, 3718-3722.
20. (n) Ohno, A.; Nakamura, K.; Shizume, Y.; Oka, S. Bull. Chem. Soc. Jpn. 1977, 50, 1003-1004.
21. (o) Masson, J.; Metzner, P.; Vialle, J. Tetrahedron 1977, 33, 3089-3095.
22. (p) Paquer, D.; Vazeux, M. J. Organomet Chem. 1977,140, 257-264.
23. 3. (a) Vedejs, E.; Perry, D. A. J. Am. Chem. Soc. 1983, 105, 1683-1684.
24. (b) Okazaki, R.; Fukuda, N.; Oyama, H.; Inamoto, N. Chem. Lett. 1984, 101-104.
25. (c) Vedejs, E.; Perry, D. A.; Wilde, R. G. J. Am. Chem. Soc. 1986,108, 2985-2989.
26. 4. (a) Walter, W.; Lüke, H. -W. Angew. Chem., Int. Ed. Engl. 1977, 16, 535-536.
27. (b) Karakasa, T.; Hanzawa, T.; Motoki, S. Bull. Chem. Soc. Jpn. 1979, 52, 3469-3470.
28. (c) Tominaga, Y.; Kohra, S.; Hosomi, A. Tetrahedron Lett. 1987, 28, 1529-1532.
29. 5. (a) Narasimhan, L.; Sanitra, R.; Swenton, J. S. J. Chem. Soc., Chem. Commun. 1978, 719-720.
30. (b) Nicolaou, K. C.; McGarry, D. G.; Somers, P. K.; Veale, C. A.; Fürst, G, T. J. Am. Chem. Soc. 1987, 109, 2504-2506.
31. 6. (a) Leger, L.; Saquet, M. C R. Acad. Sci, Ser. C 1974, 279, 695-696.
32. (b) Leger, L.; Saquet, M.; Thuillier, A.; Julia, S. J. Organomet. Chem. 1975, 96, 313-321.
33. (c) Léger, L.; Saquet, M. Bull. Soc. Chim. Fr. 1975, 657-666.
34. (d) Masson, S.; Saquet, M.; Thuillier, A. Tetrahedron Lett. 1976, 4179-4180.
35. (e) Burgot, J. -L.; Massen, J.; Vialle, J. Tetrahedron Lett. 1976, 4775-4776.
36. (f) Masson, S.; Saquet, M.; Thuillier, A. Tetrahedron 1977, 33, 2949-2954.
37. (g) Gosselin, P.; Masson, S.; Thuillier, A, J. Org. Chem. 1979, 44, 2807-2809.
38. (h) Metzner, P. J. Chem. Soc., Chem. Commun. 1982, 335-336.
39. (i) Bertz, S. H.; Dabbagh, G.; Williams, L. M. J. Org. Chem. 1985, 50, 4414-4415.
40. 7. (a) Seebach, D. Chem. Ber. 1972, 705, 487-510.
41. (b) Nilsson, N. H.; Senning, A. Chem. Ber. 1974, 107, 2345-2361.
42. (c) Saquet, M. C. R. Acad. Sci, Ser. C1976, 283, 641-644.
43. 8. Schaumann, E.; Walter, W. Chem. Ber. 1974,107, 3562-3573.
44. 9. (a) Sachs, F.; Loevy, H. Ber. Dtsch. Chem. Ges. 1903, 36, 585-588.
45. (b) Gilman, H.; Kinney, C. R. J. Am. Chem. Soc. 1924, 46, 493-497.
46. (c) Oilman, H.; Breuer, F. J. Am. Chem. Soc. 1933, 55, 1262-1264.
47. (d) Walter, W.; Bode, K. -D. Angew. Chem., Int. Ed. Engl. 1966, 5, 447-461 and references cited therein,
48. (e) Entenmann, G. Chem. -Ztg. 1977, 101, 508.
49. (f) Gosselin, P.; Masson, S.; Thuillier, A. Tetrahedron Lett. 1978, 2715-2716.
50. (g) Ito, Y.; Kobayashi, K.; Saegusa, T. Tetrahedron Lett. 1979, 1039-1042.
51. (h) Krapcho, A. P.; Stephens, W. P. J. Org. Chem. 1980, 45, 1106-1109.
52. (i) Kelly, T. R.; Echavarren, A.; Chandrakumar, N. S.; Köksal, Y. Tetrahedron Lett. 1984, 25, 2127-2130.
53. (j) Seyferth, D.; Hui, R. C. Tetrahedron Lett. 1984, 25, 5251-5254.
54. (k) Ares, J. J. Synth. Commun. 1991, 21, 625-633.
55. 10. (a) Schönberg, A.; Stephenson, A.; Kaltschmitt, H.; Petersen, E.; Schulten, H. Ber. Dtsch. Chem. Ges. 1933, 66, 237-244.
56. (b) Jensen, K. A.; Henriksen, L. Acta Chem. Scand. 1968, 22, 1107-1128.
57. (c) Meijer, J.; Vermeer, P.; Brandsma, L. Recl.: Trav. Chim. Pays-Bas 1973, 92, 601-604.
58. (d) Westmijze, H.; Kleijn, H.; Meijer, J.; Vermeer, P. Synthesis 1979, 432-434.
59. (e) Meijer, J.; Ruitenberg, K.; Westmijze, H.; Vermeer, P. Synthesis 1981, 551-554.
60. (f) Seyferth, D.; Hui, R. C. Tetrahedron Lett. 1984, 25, 2623-2626.
61. (g) Okazaki, R.; Fujii, T.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1984, 1010-1011.
62. (h) Verkruijsse, H. D.; Brandsma, L. J. Organomet. Chem. 1987, 332, 95-98.
63. (i) Ali, S. M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1989, 684-685.
64. (j) Ali, S. M.; Tanimoto, S. J. Org. Chem. 1989, 54, 5603-5607.
65. 11. (a) Okazaki, R.; Ishii, A.; Inamoto, N. Tetrahedron Lett. 1984, 25, 5147-5150.
66. (b) Guziec, F. S. Jr.; SanFilippo, L. J.; Murphy, C. J.; Moustakis, C. A.; Cullen, E. R. Tetrahedron 1985, 41, 4843-4852.
67. (c) Ishii, A.; Okazaki, R.; Inamoto, N. Bull. Chem. Soc. Jpn. 1988, 61, 861-867.
68. 12. Okazaki, R.; Kumon, N.; Inamoto, N. J. Am. Chem. Soc. 1989, 111, 5949-5951.
69. 13. (a) Okazaki, R.; Ishii, A.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1986, 71-72.
70. (b) Ishii, A.; Okazaki, R.; Inamoto, N. Bull. Chem. Soc. Jpn. 1986, 59, 2529-2535.
71. 14. Sekiguchi, M.; Ogawa, A.; Fujiwara, S.; Ryu, I.; Kambe, N.; Sonoda, N. Chem. Lett. 1990, 2053-2056.
72. 15. Jensen, K. A.; Henriksen, L. Acta Chem. Scand. 1970, 24, 3213-3229.
73. c and diphenyldiazomethane were reported, where only carbophilic adducts were obtained: (a) Regitz, M.; Hocker, J.; Schössler, W,; Weber, B.; Liedhegener, A. Justus Liebigs Ann. Chem. 1971, 748, 1-19.
74. (b) Suchar, G.; Kristian, P. Chem. Zvesti 1975, 29, 244-249; Chem. Abstr. 1975, 83, 97149e.
75. (b) Suchar, G.; Kristian, P. Chem. Zvesti 1975, 29, 244-249; Chem. Abstr. 1975, 83, 97149e.
76. (c) Becher, J.; Frandsen, E. G.; Dreier, C.; Henriksen, L. Acta Chem. Scand., Ser. B 1977, 31, 843-847.
77. (d) L'abbé, G.; Dekerk, J. -P.; Martens, C.; Toppet, S. J. Org. Chem. 1980, 45, 4366-4371.
78. 17. Sonoda, N.; Yamamoto, G.; Tsutsumi, S. Bull. Chem. Soc. Jpn. 1972, 45, 2937-2938.
79. 77Se) nor NOE enhancement by irradiation at the methyl protons of their xylyl group was observed. See: Meese, C. O.; Walter, W. Magn. Reson. Chem. 1985, 23, 327-329.
80. 19. Streitwieser, A. Jr.; Scannon, P. J.; Niemeyer, H. M. J. Am. Chem. Soc. 1972, 94, 7936-7937.
81. 20. Breslow and co-workers reported a value of 71: (a) Breslow, R.; Goodin, R. J. Am. Chem. Soc. 1976, 98, 6076-6077.
82. (b) Breslow, R.; Grant, J. L. J. Am. Chem. Soc. 1977, 99, 7745-7746.
83. (c) Jaun, B.; Schwarz, J.; Breslow, R. J. Am. Chem. Soc. 1980,102, 5741-5748.
84. But it is not comparable to the other values in Table 1. A more comparable value is about 53. See: March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Fourth Edition; John Wiley & Sons, Inc.: New York, 1992; pp. 248-253.
85. 21. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
86. 22. A concerted mechanism in which ArNC=Se bond is cleaved simultaneously as 2 attacks at Se of 1 without formation of 11 may not be ruled out yet.
87. 23. (a) Koga, N.; Koga, G.; Anselme, J. -P. Tetrahedron Lett. 1970, 3309-3312.
88. (b) Pornet, J.; Miginiac, M. L. Tetrahedron Lett. 1971, 967-970.
89. (c) Dondoni, A.; Dall'Occo, T.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Chem. Soc., Chem. Commun. 1984, 258-260.
90. (d) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Synthesis 1987, 693-696.
91. (e) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. J. Org. Chem. 1987, 52, 3413-3420.
92. 24. (a) Bortolini, O.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Heterocydes 1990, 31, 1213-1216.
93. (b) Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Heterocycles 1993, 36, 473-484.
94. 11c
95. 26. (a) Walborsky, H. M.; Niznik, G. E. J. Am. Chem. Soc. 1969, 91, 7778.
96. (b) Niznik, G. E.; Morrison, W. H. III; Walborsky, H. M. J. Org. Chem. 1974, 39, 600-604.
97. 27. It is known that reaction of isoselenocyanates with potassium selenolates proceeds in carbophilic manner, see: (a) Shafiee, A.; Fanaii, G. Synthesis 1984, 512-514.
98. (b) Zmitrovich, N. I.; Petrov, M. L.; Petrov, A. A. Zh. Org. Khim. 1990, 26, 179-184; Chem. Abstr. 1990, 113, 40575z.
99. (b) Zmitrovich, N. I.; Petrov, M. L.; Petrov, A. A. Zh. Org. Khim. 1990, 26, 179-184; Chem. Abstr. 1990, 113, 40575z.
100. 28. (a) Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831-2843.
101. (b) Bachi, M. D.; Denenmark, D. J. Am. Chem. Soc. 1989, 111, 1886-1888.
102. 29. (a) Cava, M. P.; Saris, L. E. J. Chem. Soc., Chem. Commun. 1975, 617-618.
103. (b) Meese, C. O.; Walter, W.; Mrotzek, H.; Mirzai, H. Chem. Ber. 1976, 709, 956-964.
104. 30. (a) Detty, M. R.; Wood, G. P. J. Org. Chem. 1980, 45, 80-89.
105. (b) Köhler, R.; Beyer, L.; Hantschmann, A.; Hoyer, E. Z. Chem. 1990, 30, 102-103.
106. 31. It is known that reaction of isoselenocyanates with alcoholates gives carbophilic adducts, see: (a) ref. 17
107. (b) Bertelsen F.; Gissel-Nielsen, G.; Kjær, A.; Skydstrup, T. Phytochemistry 1988, 27, 3743-3749.
108. (c) Silks, L. A. III; Peng, J.; Odom, J. D.; Dunlap, R. B. J. Chem. Soc., Perkin Trans, 1 1991, 2495-2498.
109. (d) Barton, D. H. R.; Parekh, S. I.; Tajbakhsh, M.; Theodorakis, E. A.; Tse, C. -L. Tetrahedron 1994, 50, 639-654.
110. 32. Fujiwara, S.; Shin-Ike, T.; Sonoda, N.; Aoki, M.; Okada, K.; Miyoshi, N.; Kambe, N. Tetrahedron Lett. 1991, 32, 3503-3506.
111. 33. Seebach, D.; Corey, E. J. J. Org. Chem. 1975, 40, 231-237.