Remarkable rate enhancement effect of the o-methoxy group in the nucleophilic substitution reactions at the phosphorus of phosphine-boranes

Chemistry Letters

Volumn , Issue 8, 1996, Pages 707-708

  Imamoto, Tsuneo ^a   Tsuruta, Hideyuki ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030515915     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.707     Document Type: Article

References (15)

1. T. Oshiki and T. Imamoto, Bull. Chem. Soc. Jpn., 63, 3714 (1990); T. Imamoto, T. Oshiki, T. Onozawa, M. Matsuo, T. Hikosaka, and M. Yanagawa, Heteroatom Chem., 3, 563 (1992); T. Imamoto, M. Matsuo, T. Nonomura, K. Kishikawa, and M. Yanagawa, Heteroatom Chem., 4, 475 (1993).
2. T. Oshiki and T. Imamoto, Bull. Chem. Soc. Jpn., 63, 3714 (1990); T. Imamoto, T. Oshiki, T. Onozawa, M. Matsuo, T. Hikosaka, and M. Yanagawa, Heteroatom Chem., 3, 563 (1992); T. Imamoto, M. Matsuo, T. Nonomura, K. Kishikawa, and M. Yanagawa, Heteroatom Chem., 4, 475 (1993).
3. T. Oshiki and T. Imamoto, Bull. Chem. Soc. Jpn., 63, 3714 (1990); T. Imamoto, T. Oshiki, T. Onozawa, M. Matsuo, T. Hikosaka, and M. Yanagawa, Heteroatom Chem., 3, 563 (1992); T. Imamoto, M. Matsuo, T. Nonomura, K. Kishikawa, and M. Yanagawa, Heteroatom Chem., 4, 475 (1993).
4. The reaction at refluxing temperature for 8 h using 4 equivalents of MeLi provided the product in 68% yield.
5. For recent representative examples of coordination-or chelation-controlled reactions, see the following: W. C. Still and J. H. McDonald, III, Tetrahedron Lett., 21, 1031 (1980); W. C. Still and J. A. Schneider, Tetrahedron Lett., 21, 1035 (1980); K. C. Nicolaou, D. A. Claremon, and W. E. Barnett, J. Am. Chem. Soc., 102, 6611 (1980); M. Kitamura, M. Isobe, Y. Ichikawa, and T. Goto, J. Org. Chem., 49, 3517 (1984); M. T. Reetz, Angew. Chem., Int. Ed. Engl., 23, 556 (1984); P. Beak and V. Snieckus, Acc. Chem. Res., 15, 306 (1982); H. W. Gschwend and H. R. Rodriguez, Org. React., 26, 1 (1979); V. Snieckus, Chem. Rev., 90, 879 (1990); V. Snieckus, Pure Appl. Chem., 66, 2155 (1994).
6. For recent representative examples of coordination-or chelation-controlled reactions, see the following: W. C. Still and J. H. McDonald, III, Tetrahedron Lett., 21, 1031 (1980); W. C. Still and J. A. Schneider, Tetrahedron Lett., 21, 1035 (1980); K. C. Nicolaou, D. A. Claremon, and W. E. Barnett, J. Am. Chem. Soc., 102, 6611 (1980); M. Kitamura, M. Isobe, Y. Ichikawa, and T. Goto, J. Org. Chem., 49, 3517 (1984); M. T. Reetz, Angew. Chem., Int. Ed. Engl., 23, 556 (1984); P. Beak and V. Snieckus, Acc. Chem. Res., 15, 306 (1982); H. W. Gschwend and H. R. Rodriguez, Org. React., 26, 1 (1979); V. Snieckus, Chem. Rev., 90, 879 (1990); V. Snieckus, Pure Appl. Chem., 66, 2155 (1994).
7. For recent representative examples of coordination-or chelation-controlled reactions, see the following: W. C. Still and J. H. McDonald, III, Tetrahedron Lett., 21, 1031 (1980); W. C. Still and J. A. Schneider, Tetrahedron Lett., 21, 1035 (1980); K. C. Nicolaou, D. A. Claremon, and W. E. Barnett, J. Am. Chem. Soc., 102, 6611 (1980); M. Kitamura, M. Isobe, Y. Ichikawa, and T. Goto, J. Org. Chem., 49, 3517 (1984); M. T. Reetz, Angew. Chem., Int. Ed. Engl., 23, 556 (1984); P. Beak and V. Snieckus, Acc. Chem. Res., 15, 306 (1982); H. W. Gschwend and H. R. Rodriguez, Org. React., 26, 1 (1979); V. Snieckus, Chem. Rev., 90, 879 (1990); V. Snieckus, Pure Appl. Chem., 66, 2155 (1994).
8. For recent representative examples of coordination-or chelation-controlled reactions, see the following: W. C. Still and J. H. McDonald, III, Tetrahedron Lett., 21, 1031 (1980); W. C. Still and J. A. Schneider, Tetrahedron Lett., 21, 1035 (1980); K. C. Nicolaou, D. A. Claremon, and W. E. Barnett, J. Am. Chem. Soc., 102, 6611 (1980); M. Kitamura, M. Isobe, Y. Ichikawa, and T. Goto, J. Org. Chem., 49, 3517 (1984); M. T. Reetz, Angew. Chem., Int. Ed. Engl., 23, 556 (1984); P. Beak and V. Snieckus, Acc. Chem. Res., 15, 306 (1982); H. W. Gschwend and H. R. Rodriguez, Org. React., 26, 1 (1979); V. Snieckus, Chem. Rev., 90, 879 (1990); V. Snieckus, Pure Appl. Chem., 66, 2155 (1994).
9. For recent representative examples of coordination-or chelation-controlled reactions, see the following: W. C. Still and J. H. McDonald, III, Tetrahedron Lett., 21, 1031 (1980); W. C. Still and J. A. Schneider, Tetrahedron Lett., 21, 1035 (1980); K. C. Nicolaou, D. A. Claremon, and W. E. Barnett, J. Am. Chem. Soc., 102, 6611 (1980); M. Kitamura, M. Isobe, Y. Ichikawa, and T. Goto, J. Org. Chem., 49, 3517 (1984); M. T. Reetz, Angew. Chem., Int. Ed. Engl., 23, 556 (1984); P. Beak and V. Snieckus, Acc. Chem. Res., 15, 306 (1982); H. W. Gschwend and H. R. Rodriguez, Org. React., 26, 1 (1979); V. Snieckus, Chem. Rev., 90, 879 (1990); V. Snieckus, Pure Appl. Chem., 66, 2155 (1994).
10. For recent representative examples of coordination-or chelation-controlled reactions, see the following: W. C. Still and J. H. McDonald, III, Tetrahedron Lett., 21, 1031 (1980); W. C. Still and J. A. Schneider, Tetrahedron Lett., 21, 1035 (1980); K. C. Nicolaou, D. A. Claremon, and W. E. Barnett, J. Am. Chem. Soc., 102, 6611 (1980); M. Kitamura, M. Isobe, Y. Ichikawa, and T. Goto, J. Org. Chem., 49, 3517 (1984); M. T. Reetz, Angew. Chem., Int. Ed. Engl., 23, 556 (1984); P. Beak and V. Snieckus, Acc. Chem. Res., 15, 306 (1982); H. W. Gschwend and H. R. Rodriguez, Org. React., 26, 1 (1979); V. Snieckus, Chem. Rev., 90, 879 (1990); V. Snieckus, Pure Appl. Chem., 66, 2155 (1994).
11. For recent representative examples of coordination-or chelation-controlled reactions, see the following: W. C. Still and J. H. McDonald, III, Tetrahedron Lett., 21, 1031 (1980); W. C. Still and J. A. Schneider, Tetrahedron Lett., 21, 1035 (1980); K. C. Nicolaou, D. A. Claremon, and W. E. Barnett, J. Am. Chem. Soc., 102, 6611 (1980); M. Kitamura, M. Isobe, Y. Ichikawa, and T. Goto, J. Org. Chem., 49, 3517 (1984); M. T. Reetz, Angew. Chem., Int. Ed. Engl., 23, 556 (1984); P. Beak and V. Snieckus, Acc. Chem. Res., 15, 306 (1982); H. W. Gschwend and H. R. Rodriguez, Org. React., 26, 1 (1979); V. Snieckus, Chem. Rev., 90, 879 (1990); V. Snieckus, Pure Appl. Chem., 66, 2155 (1994).
12. For recent representative examples of coordination-or chelation-controlled reactions, see the following: W. C. Still and J. H. McDonald, III, Tetrahedron Lett., 21, 1031 (1980); W. C. Still and J. A. Schneider, Tetrahedron Lett., 21, 1035 (1980); K. C. Nicolaou, D. A. Claremon, and W. E. Barnett, J. Am. Chem. Soc., 102, 6611 (1980); M. Kitamura, M. Isobe, Y. Ichikawa, and T. Goto, J. Org. Chem., 49, 3517 (1984); M. T. Reetz, Angew. Chem., Int. Ed. Engl., 23, 556 (1984); P. Beak and V. Snieckus, Acc. Chem. Res., 15, 306 (1982); H. W. Gschwend and H. R. Rodriguez, Org. React., 26, 1 (1979); V. Snieckus, Chem. Rev., 90, 879 (1990); V. Snieckus, Pure Appl. Chem., 66, 2155 (1994).
13. For recent representative examples of coordination-or chelation-controlled reactions, see the following: W. C. Still and J. H. McDonald, III, Tetrahedron Lett., 21, 1031 (1980); W. C. Still and J. A. Schneider, Tetrahedron Lett., 21, 1035 (1980); K. C. Nicolaou, D. A. Claremon, and W. E. Barnett, J. Am. Chem. Soc., 102, 6611 (1980); M. Kitamura, M. Isobe, Y. Ichikawa, and T. Goto, J. Org. Chem., 49, 3517 (1984); M. T. Reetz, Angew. Chem., Int. Ed. Engl., 23, 556 (1984); P. Beak and V. Snieckus, Acc. Chem. Res., 15, 306 (1982); H. W. Gschwend and H. R. Rodriguez, Org. React., 26, 1 (1979); V. Snieckus, Chem. Rev., 90, 879 (1990); V. Snieckus, Pure Appl. Chem., 66, 2155 (1994).
14. iPrOH), 18c: 119.0-120.5°C (MeOH). Compounds 7, 12, 14b, ISb, 16a, 16b, 17a, 17b, 19a and 19b were obtained as pasty oil.
15. B. J. Wakefield, "Organolithium Methods," Academic Press, London (1988).