Effects of phosphorus substituents on reactions of α- alkoxyphosphonium salts with nucleophiles

Chemistry - A European Journal

Volumn 18, Issue 36, 2012, Pages 11423-11432

  Goto, Akihiro ^a   Otake, Kazuki ^a   Kubo, Ozora ^a   Sawama, Yoshinari ^a   Maegawa, Tomohiro ^a   Fujioka, Hiromichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

alkoxyphosphonium salts; nucleophilic substitution; phosphines; radicals; superoxides

Indexed keywords

CO STRETCHING FREQUENCIES; CONE ANGLE; ELECTRONIC FACTORS; ELECTRONIC NATURES; ELECTRONIC PARAMETERS; GRIGNARD REAGENT; NUCLEOPHILIC SUBSTITUTION REACTIONS; NUCLEOPHILIC SUBSTITUTIONS; PHOSPHINES; RADICAL MECHANISM; RADICAL REACTIONS; RADICALS; REACTION PATHWAYS; SUPEROXIDES; TRIMETHYLSILYL;

ISOTOPES; NUCLEOPHILES; PHOSPHORUS; PHOSPHORUS COMPOUNDS; REACTION KINETICS; SUBSTITUTION REACTIONS;

SALTS;

INORGANIC SALT; ORGANOMETALLIC COMPOUND; ORGANOPHOSPHORUS COMPOUND; PHOSPHORUS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHORUS; SALTS;

EID: 84865447003     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200480     Document Type: Article

References (43)

1. S. V. Ley, B. Lygo, H. M. Organ, A. Wonnacott, Tetrahedron 1985, 41, 3825
2. W. Tückmantel, K. Oshima, K. Utimoto, Tetrahedron Lett. 1986, 27, 5617
3. S. Kim, Y. C. Kim, Synlett 1990, 115
4. E. Anders, K. Hertlein, A. Stankowiak, E. Irmer, Synthesis 1992, 577.
5. W. T. Lambert, S. D. Burke, Org. Lett. 2003, 5, 515
6. G. A. Molander, K. M. George, L. G. Monovich, J. Org. Chem. 2003, 68, 9533
7. E. Quéron, R. Lett, Tetrahedron Lett. 2004, 45, 4527
8. W. T. Lambert, G. H. Hanson, F. Benayoud, S. D. Burke, J. Org. Chem. 2005, 70, 9382
9. M. E. Jung, J. Cordova, M. Murakami, Org. Lett. 2009, 11, 3882
10. M. T. Crimmins, M. C. Mans, A. D. Rodríguez, Org. Lett. 2010, 12, 5028.
11. H. Fujioka, Y. Sawama, N. Murata, T. Okitsu, O. Kubo, S. Matsuda, Y. Kita, J. Am. Chem. Soc. 2004, 126, 11800
12. H. Fujioka, T. Okitsu, Y. Sawama, N. Murata, R. Li, Y. Kita, J. Am. Chem. Soc. 2006, 128, 5930.
13. H. Fujioka, T. Okitsu, Y. Sawama, T. Ohnaka, Y. Kita, Synlett 2006, 3077
14. H. Fujioka, T. Ohnaka, T. Okitsu, O. Kubo, K. Okamoto, Y. Sawama, Y. Kita, Heterocycles 2007, 72, 529
15. H. Fujioka, T. Okitsu, T. Ohnaka, R. Li, O. Kubo, K. Okamoto, Y. Sawama, Y. Kita, J. Org. Chem. 2007, 72, 7898
16. H. Fujioka, O. Kubo, K. Senami, K. Okamoto, T. Okitsu, Y. Kita, Heterocycles 2009, 79, 1113.
17. H. Fujioka, A. Goto, K. Otake, O. Kubo, K. Yahata, Y. Sawama, T. Maegawa, Chem. Commun. 2010, 46, 3976.
18. H. Fujioka, A. Goto, K. Otake, O. Kubo, Y. Sawama, T. Maegawa, Chem. Commun. 2011, 47, 9894.
19. C. A. Tolman, Chem. Rev. 1977, 77, 313.
20. C. W. Porter, C. Steel, J. Am. Chem. Soc. 1920, 42, 2650
21. H. Gilman, A. Wood, J. Am. Chem. Soc. 1926, 48, 806
22. M. T. Goebel, C. S. Marvel, J. Am. Chem. Soc. 1933, 55, 1693
23. M. S. Kharasch, W. B. Reynolds, J. Am. Chem. Soc. 1943, 65, 501
24. C. Walling, S. A. Buckler, J. Am. Chem. Soc. 1955, 77, 6032
25. J. F. Garst, C. D. Smith, A. C. Farrar, J. Am. Chem. Soc. 1972, 94, 7707. For a review, see
26. G. Sosnovsky, J. H. Brown, Chem. Rev. 1966, 66, 529.
27. 2 and Grignard reagents are known to produce radical anion species; see:, C. Walling, A. Cioffari, J. Am. Chem. Soc. 1970, 92, 6609; the aryl radical species coupled to itself to afford a biaryl compound, which was detected as a byproduct.
28. E. J. Corey, K. C. Nicolaou, M. Shibasaki, Y. Machida, C. S. Shiner, Tetrahedron Lett. 1975, 16, 3183
29. D. T. Sawyer, J. S. Valentine, Acc. Chem. Res. 1981, 14, 393, and references sited therein.
30. W. He, C. E. Soll, S. S. Chavadi, G. Zhang, J. D. Warren, L. E. N. Quadri, J. Am. Chem. Soc. 2009, 131, 16744.
31. G. Pandey, S. Hajra, M. K. Ghorai, K. R. Kumar, J. Org. Chem. 1997, 62, 5966.
32. A. Mendoza, D. S. Matteson, J. Organomet. Chem. 1978, 156, 149.
33. F. Ono, R. Negoro, T. Sato, Synlett 2001, 1581.
34. T. Miura, Y. Masaki, Tetrahedron 1995, 51, 10477.
35. T. Soga, H. Takenoshita, M. Yamada, T. Mukaiyama, Bull. Chem. Soc. Jpn. 1990, 63, 3122.
36. S. Hünig, H. Reichelt, Chem. Ber. 1986, 119, 1772.
37. D. E. Laycock, H. Alper, J. Org. Chem. 1981, 46, 289.
38. X. Li, L. Li, Y. Tang, L. Zhong, L. Cun, J. Zhu, J. Liao, J. Deng, J. Org. Chem. 2010, 75, 2981.
39. P. Müller, P. Nury, G. Bernardinelli, Eur. J. Org. Chem. 2001, 4137.
40. A. V. Malkov, I. R. Baxendale, D. Dvořák, D. J. Mansfield, P. Kočovský, J. Org. Chem. 1999, 64, 2737.
41. J. Karthikeyan, M. Jeganmohan, C.-H. Cheng, Chem. Eur. J. 2010, 16, 8989.
42. A. F. Trindade, P. M. P. Gois, L. F. Veiros, V. Andre, M. T. Duarte, C. A. M. Afonso, S. Caddick, F. G. N. Cloke, J. Org. Chem. 2008, 73, 4076.
43. W. S. Trahanovsky, N. S. Fox, J. Am. Chem. Soc. 1974, 96, 7968.