Face selectivity in the reactions of Grignard reagents with 5-substituted-2-dicyanomethyIeneadamantanes

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 16, 1999, Pages 2383-2390

  Kao, Kuo Hsi ^a   Siicu, Ren Shyang ^a   Clicn, Yuh Shih ^a   Lin, Wen Wci ^a   Liu, Ju Tsung ^a   Ching FaYao, ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746458853     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901484e     Document Type: Article

References (36)

1. (a) G. R. N. Jones, Nature (London), 1972,235,257;
2. (b) A. J. Fatiadi, Synthesis, 1978, 165;
3. F. Freeman, Clicm. Rev., 1980, 329.
4. (a) N. Latif and N. Mishriky, Can. J. Chem., 1966, 41, 1271;
5. (b) N. Latif, I. F. Zeid and F. Assad, Chem. Ind. (London), 1970, 1539;
6. N. Latif, N. S. Girgis and F. Michael, Tetrahedron, 1970,26,5765;
7. N. Latif, N. Mishriky and K. A. Mohsen, J. Chem. Soc., Perkin Trans. 7,1974,875.
8. (a) C. K. Cheung, L. T. Tseng, M.-H. Lin, S. Srivastava and W. J. le Noble, J. Am. Chem. Soc., 1986, 108, 1598;
9. (b) V. R. Bodepudi and W. J. le Noble, J. Org. Chem., 1991, 56, 2001; 1994, 59, 3265;
10. W.-S. Chung, T.-L.' Tsai, C.-C. Ho, M. N. N. Chiang and W. J. le Noble, J. Org. Chem., 1997, 62, 4672;
11. J. M. Coxon, K. N. Houk' and R. T. Luibrand, J. Org. Chem., 1995, 60, 418 and references cited therein.
12. (a) A. S. Cieplak, J. Am. Chem. Soc., 1981, 103, 4540;
13. (b) C. R. Johnson, B. D. Tait and A. S. Cieplak, J. Am. Chem. Soc., 1987,109, 5875;
14. A. S. Cieplak, B. D. Tait and C. R. Johnson, J. Am. Chem. Soc., 1989,111,8447.
15. (a) W. Adcock, J. Cotton and N. A. Trout, J. Org. Chem., 1994, 59, 1867;
16. (b) W. Adcock, J. Cotton and N. A. Trout, J. Org. Chem, 1995, 60,7074.
17. W. Adcock, N. J. Head, N. R. Lokan and N. A. Trout, J. Org. Chem., 1997, 62,6177.
18. (a) A. Streitwieser, C. H. Heathcock and E. M. Kosower, in Introduction to Organic Chemistry, 4th edn., Macmillan, New York, 1992, p. 403;
19. (b) M. B. Smith, in Organic Synthesis, McGraw-Hill, Singapore, 1994, p. 714;
20. J. March, in Advanced Organic Chemistry: Reactions, Mechanism and Structure, 4th edn., John Wiley & Sons, New York, 1992, p. 926.
21. M.-H. Lin, J. E. Silver and W. J. le Noble, J. Org. Chem., 1988, 53, 5155.
22. Full crystallographic details, excluding structure factor tables, have been deposited at the Cambridge Crystallographic Data Centre (CCDC). For details of the deposition scheme, see 'Instruction for Authors', J. Chem. Soc., Perkin Trans. 1, available via the RSC Web pages (http/Avww.rsc.org/authors). Any request to the CCDC for this material should quote the literature citation and the reference number 207β37. See http://www.rsc.org/suppdata/pl/1999/2383 for crystallographic files in .cif format.
23. M. S. Karasch and O. Reinmuth, Grignard Reactions of Nonmetallic Substrates, Constable, New York, 1954, p. 774.
24. E. S. Gould, Mechanism and Structure in Organic Chemistry, Holt, Rinehart and Winston, New York, 1962, p. 403.
25. P. L. Pickard and T. J. Tolbert, J. Org. Chem., 1961,26,4886.
26. C.-F. Yao, Y.-S. Chen, W.-C. Chen, R.-S. Sheu, J.-K. Lai and C.-H. Ueng, Acta Crystallogr., Sect. C, 1997,53,956.
27. V. Migrdichian, The Chemistry of Organic Cyanogen Compounds, Rêinhold, New York, 1947, p. 254.
28. (a) I. Tabushi and Y. Aoyama, J. Org. Chem., 1973, 38, 3447;
29. (b) M. Xie and W. J. le Noble, J. Org. Chem., 1989, 54, 3839;
30. W.-S. Chung, Y.-D. Liu and N.-J. Wang, J. Chem. Soc., Perkin Trans. 2, 1995, 581;
31. M. Kaselj, E. M. Gonikberg and W. J. le Noble, J. Org. Chem., 1998,63, 3218.
32. H. W. Geluk, Synthesis, 1972, 374.
33. (a) A. C. Cope and K. E. Hoyle, J. Am. Chem. Soc., 1941, 63, 733;
34. (b) B. Krijnen, H. B. Beverloo, J. W. Verhoeven, C. A. Reiss, K. Goubitz and D. Heijdenrijk, J. Am. Chem. Soc, 1989, 111, 4433.
35. A. W. J. D. Dekkers, J. W. Verhoeven and W. N. Speckamp, Tetrahedron, 1973,29, 1691.
36. R. van Hes, A. Smit, T. Kralt and A. Peters, J. Met!. Chem., 1972, 15, 132.