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Volumn 63, Issue 25, 1998, Pages 9561-9564

Sonochemical reactions of lead tetracarboxylates with styrene

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; LEAD; STYRENE;

EID: 0032509534     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981168u     Document Type: Article
Times cited : (16)

References (35)
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  • 2
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    • For general accounts on LTA reactions, see: (a) Criegee, R. In Oxidation in Organic Chemistry; Wiberg, K. B., Ed., Academic Press: New York, 1965; Part A. (b) Sheldon, R. A.; Kochi, J. K. Org. React. 1972, 19, 279-421. (c) Mihailovic, M. L.; Cekovic, Z.; Lorenc, L. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. G.; De Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; pp 741-816.
    • (1972) Org. React. , vol.19 , pp. 279-421
    • Sheldon, R.A.1    Kochi, J.K.2
  • 3
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    • Mijs, W. G.; De Jonge, C. R. H. I., Eds.; Plenum Press: New York
    • For general accounts on LTA reactions, see: (a) Criegee, R. In Oxidation in Organic Chemistry; Wiberg, K. B., Ed., Academic Press: New York, 1965; Part A. (b) Sheldon, R. A.; Kochi, J. K. Org. React. 1972, 19, 279-421. (c) Mihailovic, M. L.; Cekovic, Z.; Lorenc, L. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. G.; De Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; pp 741-816.
    • (1986) Organic Synthesis by Oxidation with Metal Compounds , pp. 741-816
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    • 0026043453 scopus 로고
    • For previous papers on this topic, see: (a) Ando, T.; Bauchat, P.; Foucaud, A.; Fujita, M.; Kimura, T.; Sohmiya, H. Tetrahedron Lett. 1991, 32, 6379-6382. (b) Ando, T.; Fujita, M.; Bauchat, P.; Foucaud, A.; Sohmiya, H.; Kimura, T. Ultrasonics Sonochemistry 1994, 1, 33-35. (c) Kimura, T.; Fujita, M.; Sohmiya, H.; Ando, T. Chem. Lett. 1995, 55-56. (d) Ando, T.; Fujita, M.; Kimura, T.; Levêque, J. M.; Luche, J. L.; Sohmiya, H. Ultrasonics Sonochemistry 1996, 3, 223-227.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 6379-6382
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    • For previous papers on this topic, see: (a) Ando, T.; Bauchat, P.; Foucaud, A.; Fujita, M.; Kimura, T.; Sohmiya, H. Tetrahedron Lett. 1991, 32, 6379-6382. (b) Ando, T.; Fujita, M.; Bauchat, P.; Foucaud, A.; Sohmiya, H.; Kimura, T. Ultrasonics Sonochemistry 1994, 1, 33-35. (c) Kimura, T.; Fujita, M.; Sohmiya, H.; Ando, T. Chem. Lett. 1995, 55-56. (d) Ando, T.; Fujita, M.; Kimura, T.; Levêque, J. M.; Luche, J. L.; Sohmiya, H. Ultrasonics Sonochemistry 1996, 3, 223-227.
    • (1994) Ultrasonics Sonochemistry , vol.1 , pp. 33-35
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  • 6
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    • For previous papers on this topic, see: (a) Ando, T.; Bauchat, P.; Foucaud, A.; Fujita, M.; Kimura, T.; Sohmiya, H. Tetrahedron Lett. 1991, 32, 6379-6382. (b) Ando, T.; Fujita, M.; Bauchat, P.; Foucaud, A.; Sohmiya, H.; Kimura, T. Ultrasonics Sonochemistry 1994, 1, 33-35. (c) Kimura, T.; Fujita, M.; Sohmiya, H.; Ando, T. Chem. Lett. 1995, 55-56. (d) Ando, T.; Fujita, M.; Kimura, T.; Levêque, J. M.; Luche, J. L.; Sohmiya, H. Ultrasonics Sonochemistry 1996, 3, 223-227.
    • (1995) Chem. Lett. , pp. 55-56
    • Kimura, T.1    Fujita, M.2    Sohmiya, H.3    Ando, T.4
  • 7
    • 0030288609 scopus 로고    scopus 로고
    • For previous papers on this topic, see: (a) Ando, T.; Bauchat, P.; Foucaud, A.; Fujita, M.; Kimura, T.; Sohmiya, H. Tetrahedron Lett. 1991, 32, 6379-6382. (b) Ando, T.; Fujita, M.; Bauchat, P.; Foucaud, A.; Sohmiya, H.; Kimura, T. Ultrasonics Sonochemistry 1994, 1, 33-35. (c) Kimura, T.; Fujita, M.; Sohmiya, H.; Ando, T. Chem. Lett. 1995, 55-56. (d) Ando, T.; Fujita, M.; Kimura, T.; Levêque, J. M.; Luche, J. L.; Sohmiya, H. Ultrasonics Sonochemistry 1996, 3, 223-227.
    • (1996) Ultrasonics Sonochemistry , vol.3 , pp. 223-227
    • Ando, T.1    Fujita, M.2    Kimura, T.3    Levêque, J.M.4    Luche, J.L.5    Sohmiya, H.6
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    • Benjamin/Cummings Publishing Company: Menlo Park, CA
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    • 84889190858 scopus 로고    scopus 로고
    • note
    • The conversion yield increases with the stirring rates (300, 600, 2400 rpm), but the relative amounts of the radical to ionic reaction products (see Table 2) is higher at 600 rpm. The parallel between ultrasonic and mechanochemical activations is not straightforward in this case.
  • 25
    • 84889193422 scopus 로고    scopus 로고
    • In addition to lactone 6, 4-phenylbutyrolactone was detected in runs 3, 4, 7, 8 in small amounts (<1%) by GC-MS spectrometry
    • In addition to lactone 6, 4-phenylbutyrolactone was detected in runs 3, 4, 7, 8 in small amounts (<1%) by GC-MS spectrometry.
  • 26
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    • note
    • 3), would give a carbocation precursor of compound 2; (ii) 13 can be transformed to 14 via an intramolecular disproportionation. The collapse of 14 would lead to the formation of 4 and a "lead(I)" species.
  • 29
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    • CRC Press: Boca Raton
    • Ionization potentials of styrene, acetic acid, and propanoic acid are 8.47, 10.69, .and 10.24 eV, respectively; Handbook of Chemistry and Physics, 69th ed.; CRC Press: Boca Raton, 1989, E 85-91.
    • (1989) Handbook of Chemistry and Physics, 69th Ed.


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