Fullerene derivatives incorporating phosphoramidous ylide and phosphoramidate: Synthesis and property

Journal of Organic Chemistry

Volumn 74, Issue 13, 2009, Pages 4866-4869

  Chen, Sheng Yuan ^a   Cheng, Rai Long ^a   Tseng, Cheng Kuo ^a   Lin, Ya Shiuan ^a   Lai, Li Hsiang ^a   Venkatachalam, Rajesh Kumar ^b   Chen, Yu Chie ^a   Cheng, Chien Hong ^b   Chuang, Shih Ching ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DIMETHYL ACETYLENEDICARBOXYLATE; ELECTROCHEMICAL STUDIES; ELECTRONIC ABSORPTION; FULLERENE DERIVATIVE; PHOSPHORAMIDATE; REDUCTIVE POTENTIAL; SIDE PRODUCTS; TRIAMIDE; VISIBLE REGION;

ABSORPTION SPECTROSCOPY; CHEMICAL REACTIONS; FULLERENES;

DERIVATIVES;

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; FULLERENE DERIVATIVE; HEMPA; HEXAETHYLPHOSPHORIC TRIAMIDE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; CYCLOADDITION; ELECTROCHEMICAL ANALYSIS; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 67649588646     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8026017     Document Type: Article

References (49)

1. (a) Hirsch, A.; Brettreich, M. Fullerenes, Chemistry and Reactions; Wiley-VCH: Weinheim, Germany, 2005.
2. (b) Perez, E. M.; Martin, N. Chem. Soc. Rev. 2008, 37, 1512-1519.
3. (c) Thilgen, C.; Diederich, F. Chem. Rev. 2006, 106, 5049-5135.
4. (d) Diederich, F.; Gomez-Lopez, M. Chimia 1998, 52, 551-556.
5. (e) Diederich, F.; Gomez-Lopez, M. Chem. Soc. Rev. 1999, 28, 263-277.
6. (f) Hirsch, A. AIP Conference Proceedings 2005, 786, 581-585.
7. (a) Tokuyama, H.; Yamago, S.; Nakamura, E.; Shiraki, T.; Sugiura, Y. J. Am. Chem. Soc. 1993, 115, 7918-7919.
8. (b) Friedman, S. H.; DeCamp, D. L.; Sijbesma, R. P.; Srdanov, G.; Wudl, F.; Kenyon, G. L. J. Am. Chem. Soc. 1993, 115, 6506-6509.
9. (c) Sijbesma, R.; Srdanov, G.; Wudl, F.; Castoro, J. A.; Wilkins, C.; Friedman, S. H.; DeCamp, D. L.; Kenyon, G. L. J. Am. Chem. Soc. 1993, 115, 6510-6512.
10. (d) Schinazi, R. F.; Sijbesma, R.; Srdanov, G.; Hill, C. L.; Wudl, F. Antimicrob. Agents Chemother. 1993, 37, 1707-1710.
11. (e) Da Ros, T.; Prato, M. Chem. Commun. 1999, 663-669.
12. (f) Wilson, S. R. Nanomedicine: Fullerene and Carbon Nanotube Biology. In Perspectives of Fullerene Nanotechnology; Osawa, E., Ed.; Kluwer Academic: Dordrecht, The Netherlands, 2002; pp 155-163.
13. (g) Berg, J. M.; Tymoczko, J. L.; Stryer, L. Biochemistry; 5th ed.; W.H. Freeman: New York, 2002; p xxxviii.
14. (a) Yamago, S.; Yanagawa, M.; Mukai, H.; Nakamura, E. Tetrahedron 1996, 52, 5091-5092.
15. (b) Yamago, S.; Yanagawa, M.; Nakamura, E. J. Chem. Soc., Chem. Commun. 1994, 2093-2094.
16. (c) Wu, S.-H.; Sun, W.-Q.; Zhang, D.-W.; Shu, L.-H.; Wu, H.-M.; Xu, J.-F.; Lao, X.-F. Tetrahedron Lett. 1998, 39, 9233-9236.
17. (d) Pellicciari, R.; Natalini, B.; Amori, L.; Marinozzi, M.; Seraglia, R. Synlett 2000, 1816-1818.
18. (e) Allard, E.; Cheng, F.; Chopin, S.; Delaunay, J.; Rondeau, D.; Cousseau, J. New J. Chem. 2003, 27, 188-192.
19. (f) Murata, Y.; Cheng, F.; Kitagawa, T.; Komatsu, K. J. Am. Chem. Soc. 2004, 126, 8874-8875.
20. (a) Nakamura, E.; Isobe, H. Acc. Chem. Res. 2003, 36, 807-815.
21. (b) A literature search of SciFinder Scholar using the keywords "water soluble fullerenes and phosphorus" gave only one reference, associated with a bone-vector study: Proceedings of Electrochemical Society by Wilson in 2002.
22. (a) Chuang, S.-C.; Santhosh, K. C.; Lin, C.-H.; Wang, S.-L.; Cheng, C.-H. J. Org. Chem. 1999, 64, 6664-6669.
23. (b) Chuang, S.-C.; Lee, D.-D.; Santhosh, K. C.; Cheng, C.-H. J. Org. Chem. 1999, 64, 8868-8872.
24. (c) Yamaguchi, H.; Murata, S.; Akasaka, T.; Suzuki, T. Tetrahedron Lett. 1997, 38, 3529-3530.
25. (a) Nakamura, E.; Isobe, H.; Tomita, N.; Sawamura, M.; Jinno, S.; Okayama, H. Angew. Chem., Int. Ed. 2000, 39, 4254-4257.
26. (b) Isobe, H.; Tomita, N.; Jinno, S.; Okayama, H.; Nakamura, E. Chem. Lett. 2001, 1214-1215.
27. (c) Isobe, H.; Nakanishi, W.; Tomita, N.; Jinno, S.; Okayama, H.; Nakamura, E. Mol. Pharm. 2006, 3, 124-134.
28. (d) Isobe, H.; Nakanishi, W.; Tomita, N.; Jinno, S.; Okayama, H.; Nakamura, E. Chem. Asian J. 2006, 1, 167-175.
29. (e) Klumpp, C.; Lacerda, L.; Chaloin, O.; Ros, T. D.; Kostarelos, K.; Prato, M.; Bianco, A. Chem. Commun. 2007, 3762-3764.
30. (f) Sitharaman, B.; Zakharian, T. Y.; Saraf, A.; Misra, P.; Ashcroft, J.; Pan, S.; Pham, Q. P.; Mikos, A. G.; Wilson, L. J.; Engler, D. A. Mol. Pharm. 2008, 5, 567-578.
31. (a) Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus - The Carbon Copy: From Organophosphorus to Phospha-organic Chemistry; Wiley: West Sussex, England, 1998.
32. (b) Corbridge, D. E. C. Phosphorus 2000: Chemistry, Biochemistry and Technology; Elsevier: New York, 2000.
33. Tran, Y. S.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 12632-12633.
34. 31P resonance at δ 33.93 ppm. See: Illa, O.; Bagan, X.; Cazorla, A. M.; Lyon, C.; Baceiredo, A.; Branchadell, V.; Ortuño, R. M. J. Org. Chem. 2006, 71, 5320-5327.
35. 4. See: (a) Denmark, S. E.; Eklov, B. M. Chem. - Eur. J. 2008, 14, 234-239.
36. (b) Bortolini, O.; Bragante, L.; Di Furia, F.; Modena, G. Can. J. Chem. 1986, 64, 1189-1195.
37. (a) Bingel, C. Chem. Ber. 1993, 126, 1957-1959.
38. (b) Hirsch, A.; Lamparth, I.; Karfunkel, H. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 437-438.
39. (a) Wang, Y.; Cheng, L. T. J. Phys. Chem. 1992, 96, 1530-1532.
40. (b) Rath, M. C.; Pal, H.; Mukherjee, T. J. Phys. Chem. A 1999, 103, 4993-5002.
41. (a) Kadish, K. M.; Ruoff, R. S. Fullerenes, Chemistry, Physics and Technology; Wiley: New York, 2000; pp 1-51.
42. (b) Suzuki, T.; Maruyama, Y.; Akasaka, T.; Ando, W.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc. 1994, 116, 1359-1363.
43. (c) Murata, Y.; Murata, M.; Komatsu, K. Chem. - Eur. J. 2003, 9, 1600-1609.
44. (d) Echegoyen, L.; Echegoyen, L. E. Acc. Chem. Res. 1998, 31, 593-601.
45. 60 and Related Compounds. Organic Electrochemistry, 4th ed.; Dekker: New York, 2001; pp 323-339.
46. (a) Murata, Y.; Motoyama, K.; Komatsu, K.; Wan, T. S. M. Tetrahedron 1996, 52, 5077-5090.
47. (b) Cheng, F.; Murata, Y.; Komatsu, K. Org. Lett. 2002, 4, 2541-2544.
48. (c) Oçafrain, M.; Herranz, M. A.; Marx, L.; Thilgen, C.; Diederich, F.; Echegoyen, L. Chem. - Eur. J. 2003, 9, 4811-4819.
49. (d) Herranz, M. A.; Diederich, F.; Echegoyen, L. Eur. J. Org. Chem. 2004, 2299-2316.