Reaction of a moderately stabilized bismuthonium ylide with 1,2-dicarbonyl compounds. A novel ring enlargement of ortho-quinones to 3-hydroxytropones

Chemical Communications

Volumn , Issue 24, 1996, Pages 2697-2698

  Matano, Yoshihiro ^a   Suzuki, Hitomi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001776301     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960002697     Document Type: Article

References (25)

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2. For reviews of organic transformations based on bismuth reagents, see. L. D. Freedman and G. O. Doak, Chem. Rev., 1982, 82, 15; J.-P. Finet, Chem. Rev., 1989, 89, 1487; M. Wada and H. Ohki, J. Synth. Org. Chem., Jpn., 1989, 47, 425: Y. Matano and H. Suzuki, Bull. Chem. Soc. Jpn., 1996, 69, 2673; H. Suzuki, T. Ikegami and Y. Matano, Synthesis, in the press.
3. For reviews of organic transformations based on bismuth reagents, see. L. D. Freedman and G. O. Doak, Chem. Rev., 1982, 82, 15; J.-P. Finet, Chem. Rev., 1989, 89, 1487; M. Wada and H. Ohki, J. Synth. Org. Chem., Jpn., 1989, 47, 425: Y. Matano and H. Suzuki, Bull. Chem. Soc. Jpn., 1996, 69, 2673; H. Suzuki, T. Ikegami and Y. Matano, Synthesis, in the press.
4. For reviews of organic transformations based on bismuth reagents, see. L. D. Freedman and G. O. Doak, Chem. Rev., 1982, 82, 15; J.-P. Finet, Chem. Rev., 1989, 89, 1487; M. Wada and H. Ohki, J. Synth. Org. Chem., Jpn., 1989, 47, 425: Y. Matano and H. Suzuki, Bull. Chem. Soc. Jpn., 1996, 69, 2673; H. Suzuki, T. Ikegami and Y. Matano, Synthesis, in the press.
5. For reviews of organic transformations based on bismuth reagents, see. L. D. Freedman and G. O. Doak, Chem. Rev., 1982, 82, 15; J.-P. Finet, Chem. Rev., 1989, 89, 1487; M. Wada and H. Ohki, J. Synth. Org. Chem., Jpn., 1989, 47, 425: Y. Matano and H. Suzuki, Bull. Chem. Soc. Jpn., 1996, 69, 2673; H. Suzuki, T. Ikegami and Y. Matano, Synthesis, in the press.
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10. For the C-C bond formations based on stabilized bismuthonium ylides, see: H. Suzuki, T. Murafuji and T. Ogawa, Chem. Lett., 1988, 847; T. Ogawa, T. Murafuji and H. Suzuki, Chem. Lett., 1989, 849; T. Ogawa, T. Murafuji and H. Suzuki, J. Chem. Soc., Chem. Commun., 1989, 1749; T. Ogawa, T. Murafuji, K. Iwata and H. Suzuki, Chem. Lett., 1989, 325.
11. For the C-C bond formations based on stabilized bismuthonium ylides, see: H. Suzuki, T. Murafuji and T. Ogawa, Chem. Lett., 1988, 847; T. Ogawa, T. Murafuji and H. Suzuki, Chem. Lett., 1989, 849; T. Ogawa, T. Murafuji and H. Suzuki, J. Chem. Soc., Chem. Commun., 1989, 1749; T. Ogawa, T. Murafuji, K. Iwata and H. Suzuki, Chem. Lett., 1989, 325.
12. For the C-C bond formations based on stabilized bismuthonium ylides, see: H. Suzuki, T. Murafuji and T. Ogawa, Chem. Lett., 1988, 847; T. Ogawa, T. Murafuji and H. Suzuki, Chem. Lett., 1989, 849; T. Ogawa, T. Murafuji and H. Suzuki, J. Chem. Soc., Chem. Commun., 1989, 1749; T. Ogawa, T. Murafuji, K. Iwata and H. Suzuki, Chem. Lett., 1989, 325.
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20. For the known ring expansion reactions of ortho-quinones to tropones and tropolones, see: B. Eistert and L. Klein, Chem. Ber., 1968, 101, 391; M. Sato, J. Tsunetsugu and S. Ebine, Bull. Chem. Soc. Jpn., 1972, 45, 638; H. Kogler, H.-W. Fehlhaber, K. Leube and W. Durckheimer, Chem. Ber., 1989, 122, 2205.
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22. Triphenylphosphonium 2-oxoalkylides undergo the Wittig reaction with 9,10-phenanthroquinone to give α,β-unsaturated ketones as the initial product, see D. N. Nicolaides, S. G. Adamopoulos, D. A. Lefkaditis, K. E. Litinas and P. V. Tarantili, J. Chem. Soc., Perkin Trans. 1, 1992, 283;
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