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Volumn 62, Issue 26, 1997, Pages 9314-9317

Synthesis of Halomethyl and Other Bipyridine Derivatives by Reaction of 4,4′-Bis[(trimethylsilyl)methyl]-2,2′-bipyridine with Electrophiles in the Presence of Fluoride Ion

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EID: 0000170479     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971685x     Document Type: Article
Times cited : (64)

References (46)
  • 1
    • 0001827606 scopus 로고
    • Wilkinson, Sir G.; Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford and NY, and references therein
    • Reedijk, J. In Comprehensive Coordination Chemistry; Wilkinson, Sir G.; Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford and NY, 1987; Vol. 2, pp 73-98 and references therein.
    • (1987) Comprehensive Coordination Chemistry , vol.2 , pp. 73-98
    • Reedijk, J.1
  • 6
    • 0031040846 scopus 로고    scopus 로고
    • and references therein
    • (e) See: Tzalis, D.; Tor, Y. J. Am. Chem. Soc. 1997, 119, 852-3 and references therein.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 852-853
    • Tzalis, D.1    Tor, Y.2
  • 30
    • 85034475054 scopus 로고    scopus 로고
    • note
    • 3 produced the less reactive dichloro product 3 in impure form.
  • 36
    • 85034471311 scopus 로고    scopus 로고
    • note
    • 2, 3.5% EtOAc in hexanes, TMS compound elutes first) or more conveniently, by recrystallization from a minimal amount of hexanes at -4°C. The TMS bpy 1 precipitates and may be collected by filtration. The yellow impurity may be removed from the solid thus collected by washing with copious quantities of very cold hexanes, leaving the TMS product 1 as a white crystalline solid.
  • 37
    • 85034477506 scopus 로고    scopus 로고
    • note
    • 3, followed by concentration of the organic layer.
  • 39
    • 85034459284 scopus 로고    scopus 로고
    • note
    • 2Br: bp = 47°C), but also leads to side products and depressed yields in the alkylation reactions as compared with reactions run in DMF solution.
  • 40
    • 85034463505 scopus 로고    scopus 로고
    • note
    • Though the phenethyl product 7 is produced in good yield (83%, GC) by the CsF reaction, this drops dramatically during purification due to the difficulties of separation from the dimethyl bpy byproduct of similar polarity.
  • 44
    • 85034469323 scopus 로고    scopus 로고
    • Rotoevaporation at elevated temperature results in decomposition of the "dry TBAF" reagent
    • Rotoevaporation at elevated temperature results in decomposition of the "dry TBAF" reagent.
  • 46
    • 85034479179 scopus 로고    scopus 로고
    • Melting points in ref 20a for mono- and dialkylated products appear to be transposed. The melting point reported for the monoalkyl bpy (76-77°C) is coincident with what we measured for the dialkylated product
    • Melting points in ref 20a for mono- and dialkylated products appear to be transposed. The melting point reported for the monoalkyl bpy (76-77°C) is coincident with what we measured for the dialkylated product.


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