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Volumn 73, Issue 22, 2008, Pages 9140-9143

Cooperative effect of carborane and pyridine in the reaction of carboranyl alcohols with thionyl chloride: Halogenation versus oxidation

Author keywords

[No Author keywords available]

Indexed keywords

HALOGENATION; SULFUR COMPOUNDS;

EID: 56449101536     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801672f     Document Type: Article
Times cited : (23)

References (35)
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    • Teixidor, F.1    Viñas, C.2
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    • (1979) Comprehensive Organic Chemistry , vol.1 , pp. 493
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    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 203
    • Bohlmann, R.1
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    • Hudlicky, T. In Chemistry of Functional Groups; Patai, S., Rapport, Z., Eds.; Wiley: New York, 1983; p 1021.
    • (c) Hudlicky, T. In Chemistry of Functional Groups; Patai, S., Rapport, Z., Eds.; Wiley: New York, 1983; p 1021.
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    • Paquette, L. A, Ed, Wiley: Chichester, UK
    • (c) Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, UK, 1995; Vol 7, p 4873.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.7 , pp. 4873
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    • 3).
    • 3).
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    • See for example: a
    • See for example: (a) Tsuji, M. J. Org. Chem. 2004, 69, 4063.
    • (2004) J. Org. Chem , vol.69 , pp. 4063
    • Tsuji, M.1
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    • 2.
    • 2.
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    • Leaving the reaction mixture to stand at room temperature for several hours resulted in the precipitation of the pyridinium salt 2a·HCl. The latter has been fully characterized SI
    • Leaving the reaction mixture to stand at room temperature for several hours resulted in the precipitation of the pyridinium salt 2a·HCl. The latter has been fully characterized (SI).
  • 31
    • 56449128768 scopus 로고    scopus 로고
    • 5th ed, Smith, M. B, March, J, Eds, Wiley Interscience: New York, and
    • (a) March's Advanced Organic Chemistry, 5th ed.; Smith, M. B., March, J., Eds.; Wiley Interscience: New York, 2001; pp 469 and 576.
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  • 35
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    • 2 by NMR clearly shows the fast formation of a pyridinium salt (d 16.4 br s, 1H) as the sole product at room temperature. Further heating or addition of a base gives the final chloro derivative (SI).
    • 2 by NMR clearly shows the fast formation of a pyridinium salt (d 16.4 br s, 1H) as the sole product at room temperature. Further heating or addition of a base gives the final chloro derivative (SI).


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