Nucleophilic substitution by Grignard reagents on sulfur mustards

Journal of Organic Chemistry

Volumn 69, Issue 21, 2004, Pages 7336-7339

  Converse, Antonella ^a   Saaidi, Pierre Loïc ^a,b   Sharpless, K Barry ^a   Finn, M G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITÉ DE LYON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; MAGNESIUM PRINTING PLATES; SCAFFOLDS;

GRIGNARD REAGENTS; ORGANOMAGNESIUM NUCLEOPHILES; SULFUR MUSTARDS;

SULFUR;

2,6 DICHLORO 9 THIABICYCLO[3.3.1]NONANE; MUSTARD GAS; REAGENT; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CRYSTAL STRUCTURE; GRIGNARD REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

CRYSTALLOGRAPHY, X-RAY; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; MUSTARD COMPOUNDS; OXIDATION-REDUCTION; STEREOISOMERISM; SULFUR;

EID: 5444243849     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0489869     Document Type: Article

References (32)

1. Weil, E. D.; Smith, K. J.; Gruber, R. J. J. Org. Chem. 1966, 31, 1669-1679.
2. Converse, A.; Burow, K.; Marzinzik, A.; Sharpless, K. B.; Finn, M. G. J. Org. Chem. 2001, 66, 4386-4392.
3. Smoliakova, I. P.; Caple, R.; Brenny, J. W.; Smit, W. A.; Kryschenko, Y. K.; Shashkov, A. S.; Chizhov, O. S.; Krimer, M. Z.; Morar, G. V.; Kalyan, Y. B. Synlett 1995, 275-276 and references therein.
4. Tolstikov, G. A.; Kantyukova, R. G.; Spirikhin, L. V. Zh. Org. Kim. 1980, 16, 1408-1418.
5. (a) Examples include the following: (i) Fuji, K.; Tanaka, K; Ahn, M.; Mizuchi, M. Chem. Pharm. Bull. 1994, 42, 957-959.
6. (ii) Calo, V.; De Nitti, C.; Lopez, L.; Scilimati, A. Tetrahedron 1992, 48, 6051-6058.
7. (iii) Oliva, M.; Safont, V. S.; Andres, J.; Castillo, R.; Moliner, V. Int. J. Quantum Chem. 1997, 65, 719-728.
8. (b) An ambiguous case is provided by: Marot, C.; Philipp, C.; Rollin, P. Tetrahedron Lett. 1992, 33, 4575-4578. It is not clear which phenomenon - tethered reactivity or true anchimeric assistance - is operative in the examples described.
9. (a) Smoliakova, I. P.; Han, M. M.; Gong, J. C. Tetrahedron 1999, 55, 4559-4572.
10. (b) Han, M. M.; Smoliakova, I. P.; Koikov, L. N. Carbohydr. Res. 2000, 323, 202-207.
11. (c) Smoliakova, I. P. Curr. Org. Chem. 2000, 4, 589-608.
12. (d) Liu, H.; Smoliakova, I. P. Tetrahedron 2001, 57, 2973-2980.
13. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Tymoshenko, D. O.; Belyakov, S. A. Synthesis 1999, Supplment, 1437-1440.
14. Brown, W. A. C.; Eglinton, G.; Martin, J.; Parker, W.; Sim, G. A. Proc. Chem. Soc. 1964, 57-58.
15. Keck, G. E.; Andrus, M. B.; Romer, D. R. J. Org. Chem. 1991, 56, 417-420.
16. McManus, S. P.; Karaman, R. M.; Sedaghat-Herati, R.; Harris, J. M. J. Org. Chem. 1995, 60, 4764-4766.
17. 2 in nonpolar solvents. In addition, the best reaction conditions (high concentration in nonpolar solvent) lend themselves to the formation of oligomers, which are less basic than monomeric Grignard reagents. See: Silverman, G. S. In Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker Inc.: New York, 1996; pp 307-353.
18. Krow, G. R.; Lin, G.; Rapolu, D.; Fang, Y.; Lester, W. S.; Herzon, S. B.; Sonnet, P. E. J. Org. Chem. 2003, 68, 5292-5299.
19. Gajewski, J. J. J. Am. Chem. Soc. 2001, 123, 10877-10883.
20. (a) Ganellin, C. R.; Hollyman, D. R.; Ridley, H. F. J. Chem. Soc. C 1967, 2220-2225.
21. (b) Ring opening of aziridinium electrophiles with Grignard reagents has been reported, in a two-step sequence rather than as a case of anchimeric assistance: Draper, R. W.; Hou, D.; Iyer, R.; Lee, G. M.; Liang, J. T.; Mas, J. L.; Tormos, W.; Vater, E. J.; Guenter, F.; Mergelsberg, I.; Scherer, D. Org. Proc. Res. Dev. 1998, 2, 175-185.
22. (a) Frisch, A. C.; Shaikh, N.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2002, 41, 4056-4059.
23. (b) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686-3687.
24. (c) Nagano, T.; Hayashi, T. Org. Lett. 2004, 6, 1297-1299.
25. (d) Scheiper, B.; Bonnekessel, M.; Krause, H.; Furstner, A. J. Org. Chem. 2004, 69, 3943-3949.
26. (e) Yang, L.-M.; Huang, L.-F.; Luh, T.-Y. Org. Lett. 2004, 6, 1461-1463.
27. (f) Terao, J.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2003, 125, 5646-5647.
28. (g) Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137-4139.
29. (h) Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222-4223.
30. (i) Dohle, W.; Lindsay, D. M.; Knochel, P. Org. Lett. 2001, 3, 2871-2873.
31. (j) Shimizu, R.; Yoneda, E.; Fuchikami, T. Tetrahedron Lett. 1996, 37, 5557-5560.
32. (k) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.