Synthesis and reaction of unsymmetrical tetraarylbismuthonium salts. First isolation of bismuthonium salts bearing all different aryl groups

Chemistry Letters

Volumn , Issue 2, 1998, Pages 127-128

  Matano, Yoshihiro ^a   Miyamatsu, Takashi ^a   Suzuki, Hitomi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032395637     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.127     Document Type: Article

References (25)

1. For reviews on the chemistry of polyarylated hypervalent heteroatom compounds, see: D. Hellwinkel, Top. Curr. Chem., 109, 1 (1983); J.-P. Finet, Chem. Rev., 89, 1487 (1989); G. F. Koser, in "The Chemistry of Functional Groups, Suppl. D," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1983), Chap. 18, p.721; N. Furukawa, in "Heteroatom Chemistry," ed by E. Block, VCH (1990), Chap. 9, p.165; R. Burgada and R. Setton, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 3, p. 185; S. Oae, Pure Appl. Chem., 68, 805 (1996); K.-y. Akiba, Pure Appl. Chem., 68, 837 (1996), and references cited therein.
2. For reviews on the chemistry of polyarylated hypervalent heteroatom compounds, see: D. Hellwinkel, Top. Curr. Chem., 109, 1 (1983); J.-P. Finet, Chem. Rev., 89, 1487 (1989); G. F. Koser, in "The Chemistry of Functional Groups, Suppl. D," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1983), Chap. 18, p.721; N. Furukawa, in "Heteroatom Chemistry," ed by E. Block, VCH (1990), Chap. 9, p.165; R. Burgada and R. Setton, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 3, p. 185; S. Oae, Pure Appl. Chem., 68, 805 (1996); K.-y. Akiba, Pure Appl. Chem., 68, 837 (1996), and references cited therein.
3. For reviews on the chemistry of polyarylated hypervalent heteroatom compounds, see: D. Hellwinkel, Top. Curr. Chem., 109, 1 (1983); J.-P. Finet, Chem. Rev., 89, 1487 (1989); G. F. Koser, in "The Chemistry of Functional Groups, Suppl. D," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1983), Chap. 18, p.721; N. Furukawa, in "Heteroatom Chemistry," ed by E. Block, VCH (1990), Chap. 9, p.165; R. Burgada and R. Setton, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 3, p. 185; S. Oae, Pure Appl. Chem., 68, 805 (1996); K.-y. Akiba, Pure Appl. Chem., 68, 837 (1996), and references cited therein.
4. For reviews on the chemistry of polyarylated hypervalent heteroatom compounds, see: D. Hellwinkel, Top. Curr. Chem., 109, 1 (1983); J.-P. Finet, Chem. Rev., 89, 1487 (1989); G. F. Koser, in "The Chemistry of Functional Groups, Suppl. D," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1983), Chap. 18, p.721; N. Furukawa, in "Heteroatom Chemistry," ed by E. Block, VCH (1990), Chap. 9, p.165; R. Burgada and R. Setton, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 3, p. 185; S. Oae, Pure Appl. Chem., 68, 805 (1996); K.-y. Akiba, Pure Appl. Chem., 68, 837 (1996), and references cited therein.
5. For reviews on the chemistry of polyarylated hypervalent heteroatom compounds, see: D. Hellwinkel, Top. Curr. Chem., 109, 1 (1983); J.-P. Finet, Chem. Rev., 89, 1487 (1989); G. F. Koser, in "The Chemistry of Functional Groups, Suppl. D," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1983), Chap. 18, p.721; N. Furukawa, in "Heteroatom Chemistry," ed by E. Block, VCH (1990), Chap. 9, p.165; R. Burgada and R. Setton, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 3, p. 185; S. Oae, Pure Appl. Chem., 68, 805 (1996); K.-y. Akiba, Pure Appl. Chem., 68, 837 (1996), and references cited therein.
6. For reviews on the chemistry of polyarylated hypervalent heteroatom compounds, see: D. Hellwinkel, Top. Curr. Chem., 109, 1 (1983); J.-P. Finet, Chem. Rev., 89, 1487 (1989); G. F. Koser, in "The Chemistry of Functional Groups, Suppl. D," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1983), Chap. 18, p.721; N. Furukawa, in "Heteroatom Chemistry," ed by E. Block, VCH (1990), Chap. 9, p.165; R. Burgada and R. Setton, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 3, p. 185; S. Oae, Pure Appl. Chem., 68, 805 (1996); K.-y. Akiba, Pure Appl. Chem., 68, 837 (1996), and references cited therein.
7. For reviews on the chemistry of polyarylated hypervalent heteroatom compounds, see: D. Hellwinkel, Top. Curr. Chem., 109, 1 (1983); J.-P. Finet, Chem. Rev., 89, 1487 (1989); G. F. Koser, in "The Chemistry of Functional Groups, Suppl. D," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1983), Chap. 18, p.721; N. Furukawa, in "Heteroatom Chemistry," ed by E. Block, VCH (1990), Chap. 9, p.165; R. Burgada and R. Setton, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 3, p. 185; S. Oae, Pure Appl. Chem., 68, 805 (1996); K.-y. Akiba, Pure Appl. Chem., 68, 837 (1996), and references cited therein.
8. Chiral polyarylated phosphonium and arsonium salts, see: R. Luckenbach, Phosphorus, 1, 223, 229, 293 (1972); D. G. Allen, N. K. Roberts, and S. B. Wild, J. Chem. Soc., Chem. Commun., 1978, 346; D. G. Allen, C. L. Raston, B. W. Skelton, A. H. White, and S. B. Wild, Aust. J. Chem., 37, 1171 (1984); H.-J. Cristau and F. Plénat, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 2, p. 45; S. B. Wild, in "The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds," ed by S. Patai, Wiley, Chichester (1994), Chap. 3, p.89, and references cited therein.
9. Chiral polyarylated phosphonium and arsonium salts, see: R. Luckenbach, Phosphorus, 1, 223, 229, 293 (1972); D. G. Allen, N. K. Roberts, and S. B. Wild, J. Chem. Soc., Chem. Commun., 1978, 346; D. G. Allen, C. L. Raston, B. W. Skelton, A. H. White, and S. B. Wild, Aust. J. Chem., 37, 1171 (1984); H.-J. Cristau and F. Plénat, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 2, p. 45; S. B. Wild, in "The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds," ed by S. Patai, Wiley, Chichester (1994), Chap. 3, p.89, and references cited therein.
10. Chiral polyarylated phosphonium and arsonium salts, see: R. Luckenbach, Phosphorus, 1, 223, 229, 293 (1972); D. G. Allen, N. K. Roberts, and S. B. Wild, J. Chem. Soc., Chem. Commun., 1978, 346; D. G. Allen, C. L. Raston, B. W. Skelton, A. H. White, and S. B. Wild, Aust. J. Chem., 37, 1171 (1984); H.-J. Cristau and F. Plénat, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 2, p. 45; S. B. Wild, in "The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds," ed by S. Patai, Wiley, Chichester (1994), Chap. 3, p.89, and references cited therein.
11. Chiral polyarylated phosphonium and arsonium salts, see: R. Luckenbach, Phosphorus, 1, 223, 229, 293 (1972); D. G. Allen, N. K. Roberts, and S. B. Wild, J. Chem. Soc., Chem. Commun., 1978, 346; D. G. Allen, C. L. Raston, B. W. Skelton, A. H. White, and S. B. Wild, Aust. J. Chem., 37, 1171 (1984); H.-J. Cristau and F. Plénat, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 2, p. 45; S. B. Wild, in "The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds," ed by S. Patai, Wiley, Chichester (1994), Chap. 3, p.89, and references cited therein.
12. Chiral polyarylated phosphonium and arsonium salts, see: R. Luckenbach, Phosphorus, 1, 223, 229, 293 (1972); D. G. Allen, N. K. Roberts, and S. B. Wild, J. Chem. Soc., Chem. Commun., 1978, 346; D. G. Allen, C. L. Raston, B. W. Skelton, A. H. White, and S. B. Wild, Aust. J. Chem., 37, 1171 (1984); H.-J. Cristau and F. Plénat, in "The Chemistry of Organophosphorus Compounds," ed by F. R. Hartley, Wiley, Chichester (1994), Vol. 3, Chap. 2, p. 45; S. B. Wild, in "The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds," ed by S. Patai, Wiley, Chichester (1994), Chap. 3, p.89, and references cited therein.
13. D. Hellwinkel and M. Bach, Liebigs Ann. Chem., 720, 198 (1968).
14. For the synthesis of unsymmetrical alkyltriarylbismuthonium salts, see: R. G. Goel and H. S. Prasad, J. Chem. Soc. A, 1971, 562; Y. Matano, N. Azuma, and H. Suzuki, J. Chem. Soc., Perkin Trans. 1, 1994, 1739; Y. Matano, N. Azuma, and H. Suzuki, J. Chem. Soc., Perkin Trans. 1, 1995, 2543; Y. Matano and H. Suzuki, Bull. Chem. Soc. Jpn., 69, 2673 (1996), and references cited therein.
15. For the synthesis of unsymmetrical alkyltriarylbismuthonium salts, see: R. G. Goel and H. S. Prasad, J. Chem. Soc. A, 1971, 562; Y. Matano, N. Azuma, and H. Suzuki, J. Chem. Soc., Perkin Trans. 1, 1994, 1739; Y. Matano, N. Azuma, and H. Suzuki, J. Chem. Soc., Perkin Trans. 1, 1995, 2543; Y. Matano and H. Suzuki, Bull. Chem. Soc. Jpn., 69, 2673 (1996), and references cited therein.
16. For the synthesis of unsymmetrical alkyltriarylbismuthonium salts, see: R. G. Goel and H. S. Prasad, J. Chem. Soc. A, 1971, 562; Y. Matano, N. Azuma, and H. Suzuki, J. Chem. Soc., Perkin Trans. 1, 1994, 1739; Y. Matano, N. Azuma, and H. Suzuki, J. Chem. Soc., Perkin Trans. 1, 1995, 2543; Y. Matano and H. Suzuki, Bull. Chem. Soc. Jpn., 69, 2673 (1996), and references cited therein.
17. For the synthesis of unsymmetrical alkyltriarylbismuthonium salts, see: R. G. Goel and H. S. Prasad, J. Chem. Soc. A, 1971, 562; Y. Matano, N. Azuma, and H. Suzuki, J. Chem. Soc., Perkin Trans. 1, 1994, 1739; Y. Matano, N. Azuma, and H. Suzuki, J. Chem. Soc., Perkin Trans. 1, 1995, 2543; Y. Matano and H. Suzuki, Bull. Chem. Soc. Jpn., 69, 2673 (1996), and references cited therein.
18. 2: C, 45.50; H, 3.54%.
19. 4] was the initially formed species, see: Y, Matano, M. Yoshimune, N. Azuma, and H. Suzuki, J. Chem. Soc., Perkin Trans. 1, 1996, 1971. Stang et al. prepared some unsymmetrical iodonium salts using [PhICN][OTf] and organotin reagents, see: B. L. Williamson, R. R. Tykwinski, and P. J. Stang, J. Am. Chem. Soc., 116, 93 (1994), and references cited therein.
20. 4] was the initially formed species, see: Y, Matano, M. Yoshimune, N. Azuma, and H. Suzuki, J. Chem. Soc., Perkin Trans. 1, 1996, 1971. Stang et al. prepared some unsymmetrical iodonium salts using [PhICN][OTf] and organotin reagents, see: B. L. Williamson, R. R. Tykwinski, and P. J. Stang, J. Am. Chem. Soc., 116, 93 (1994), and references cited therein.
21. 2 with KF.
22. Y. Matano, T. Miyamatsu, and H. Suzuki, Organometallics, 15, 1951 (1996).
23. 3) spectrum of which showed no diastereotopically separated signals. Addition of europium tris(heptafluorobutanoyl-pivaloylmethanate) did not cause the separation of the signals. At present, it is not clear whether this is due to slight difference in the steric environment around the aryl ligands between two diastereomers or due to the formation of a single diastereomer. Studies on the isolation and isomerization of optically active bismuthonium compounds are now under way.
24. 4)Bi (R = Me, MeO) were also formed; their yields approximately paralleled with the respective yields of 4b,c and 4a.
25. D. H. R. Barton, N. Y. Bhatnagar, J.-P. Finct, and W. B. Motherwell, Tetrahedron, 42, 3111 (1986).