Acid mediated phosphine-borane decomplexation: A model for characterizing short-lived intermediates with experimental and ab initio NMR data

Journal of Organic Chemistry

Volumn 65, Issue 7, 2000, Pages 2261-2263

  McKinstry, Lydia ^a   Overberg, Jennifer J ^a   Soubra Ghaoui, Chirine ^a   Walsh, Darron S ^a   Robins, K A ^a   Toto, Teressa Tangredi ^b   Toto, Joseph L ^b  

^a UNIVERSITY OF NEVADA   (United States)

^b SALVE REGINA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; PHOSPHINE;

CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; MODEL; NOTE; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034616405     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9919456     Document Type: Note

References (27)

1. For recent reviews on phosphine-borane chemistry, see: Ohff, M.; Holz, J.; Quirmbach, M.; Borner, A. Synthesis 1998, 1391. Carboni, B.; Monnier, L. Tetrahedron 1999, 55, 1197.
2. For recent reviews on phosphine-borane chemistry, see: Ohff, M.; Holz, J.; Quirmbach, M.; Borner, A. Synthesis 1998, 1391. Carboni, B.; Monnier, L. Tetrahedron 1999, 55, 1197.
3. (a) Imamoto, T.; Hikosaka, T. J. Org. Chem. 1994, 59, 6753.
4. (b) Imamoto, T.; Hirakawa, E.; Yamanoi, Y.; Inoue, T.; Yamaguchi, K.; Seki, H. J. Org. Chem. 1995, 60, 7697 and references.
5. (a) Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.
6. (b) Imamoto, T. Pure Appl. Chem. 1993, 65, 655, and references.
7. Gaumont, A. C.; Bourumeau, K.; Denis, J. M.; Guenot, P. J. Organomet. Chem. 1994, 484, 9.
8. For additional synthetic methods, see: Gamble, E. L.; Gilmont, P. J. Am. Chem. Soc. 1940, 62, 717. Baldwin, R. A.; Washburn, R. M. J. Org. Chem. 1961, 26, 3549. Nainan, K. C.; Ryschkewitsch, G. E. Inorg. Chem. 1969, 8, 2671. Mathur, M. A.; Myers, W. H.; Sisler, H. H.; Ryschkewitsch, G. E. Inorg. Synth. 1974, 15, 128.
9. For additional synthetic methods, see: Gamble, E. L.; Gilmont, P. J. Am. Chem. Soc. 1940, 62, 717. Baldwin, R. A.; Washburn, R. M. J. Org. Chem. 1961, 26, 3549. Nainan, K. C.; Ryschkewitsch, G. E. Inorg. Chem. 1969, 8, 2671. Mathur, M. A.; Myers, W. H.; Sisler, H. H.; Ryschkewitsch, G. E. Inorg. Synth. 1974, 15, 128.
10. For additional synthetic methods, see: Gamble, E. L.; Gilmont, P. J. Am. Chem. Soc. 1940, 62, 717. Baldwin, R. A.; Washburn, R. M. J. Org. Chem. 1961, 26, 3549. Nainan, K. C.; Ryschkewitsch, G. E. Inorg. Chem. 1969, 8, 2671. Mathur, M. A.; Myers, W. H.; Sisler, H. H.; Ryschkewitsch, G. E. Inorg. Synth. 1974, 15, 128.
11. For additional synthetic methods, see: Gamble, E. L.; Gilmont, P. J. Am. Chem. Soc. 1940, 62, 717. Baldwin, R. A.; Washburn, R. M. J. Org. Chem. 1961, 26, 3549. Nainan, K. C.; Ryschkewitsch, G. E. Inorg. Chem. 1969, 8, 2671. Mathur, M. A.; Myers, W. H.; Sisler, H. H.; Ryschkewitsch, G. E. Inorg. Synth. 1974, 15, 128.
12. (a) Brisset, H.; Gourdel, Y.; Pellon, P.; Le Corre, M. Tetrahedron Lett. 1993, 34, 4523.
13. (b) Yamago, S.; Yanagawa, M.; Nakamura, E. J. Chem. Soc., Chem. Commun. 1994, 2093.
14. McKinstry, L.; Livinghouse, T. Tetrahedron Lett. 1994, 35, 9319.
15. McKinstry, L.; Livinghouse, T. Tetrahedron 1995, 51, 7655.
16. (e) Langer, F.; Knochel, P. Tetrahedron Lett. 1995, 36, 4591.
17. (f) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 6565.
18. (a) Imamoto, T.; Oshiki, T. Tetrahedron Lett. 1989, 30, 383.
19. (b) Oshiki, T.; Imamoto, T. Bull. Chem. Soc. Jpn. 1990, 63, 2846.
20. Gaussian 98: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.;; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gausaian, Inc., Pittsburgh, PA, 1998.
21. Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497.
22. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
23. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
24. This approach was shown to give good results in studies by Chesnut and Phung: (a) Chesnut, D. B. J. Comput. Chem. 1989, 10, 648. (b) Chesnut, D. B.; Phung, C. G. Chem. Phys. Lett. 1991, 183, 505. Chesnut, D. B. J. Comput. Chem. 1994, 14, 1364.
25. This approach was shown to give good results in studies by Chesnut and Phung: (a) Chesnut, D. B. J. Comput. Chem. 1989, 10, 648. (b) Chesnut, D. B.; Phung, C. G. Chem. Phys. Lett. 1991, 183, 505. Chesnut, D. B. J. Comput. Chem. 1994, 14, 1364.
26. This approach was shown to give good results in studies by Chesnut and Phung: (a) Chesnut, D. B. J. Comput. Chem. 1989, 10, 648. (b) Chesnut, D. B.; Phung, C. G. Chem. Phys. Lett. 1991, 183, 505. Chesnut, D. B. J. Comput. Chem. 1994, 14, 1364.
27. Better comparisons to experiment could require various consideration neglected in this study, such as molecular rotational, vibrational, and solvent effects. For a recent review, see: Helgaker, T.; Jaszunski, M.; Ruud, K. Chem. Rev. 1999, 99, 293.