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Volumn 48, Issue 33, 2007, Pages 5761-5765

A direct functionalization of tertiary alkyl bromides with O-, N-, and C-nucleophiles

Author keywords

Nucleophile; Quaternary; Silver oxide; Steric hindrance; Tertiary bromide

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; BROMINE DERIVATIVE; CARBON; CARBOXYLIC ACID DERIVATIVE; ETHER DERIVATIVE; FUNCTIONAL GROUP; HYDROCARBON; NITROGEN; OXYGEN; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILVER; TERTIARY ALKYL GROUP;

EID: 34447528830     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.091     Document Type: Article
Times cited : (8)

References (17)
  • 1
    • 33846446745 scopus 로고    scopus 로고
    • For a recent review, see:
    • For a recent review, see:. Peters K.S. Acc. Chem. Res. 40 (2007) 1
    • (2007) Acc. Chem. Res. , vol.40 , pp. 1
    • Peters, K.S.1
  • 6
    • 34447548124 scopus 로고    scopus 로고
    • note
    • A single example of a phenol addition has been reported in ref. 2b yielding the desired α-phenoxyamide in 50% yield in 3 days. We were unable to reproduce this result; please see Table 1 for details.
  • 11
    • 34447567800 scopus 로고    scopus 로고
    • note
    • While the selectivity and the rate of the model reaction remained unchanged with increasing water content, aqueous fraction significantly higher then 5% of the reaction media caused precipitation of 2a and 3a. For practical applications, acetonitrile/water ratio of 95/5 proved optimal.
  • 12
    • 34447557280 scopus 로고    scopus 로고
    • note
    • 13C NMR, LCMS, and HRMS.
  • 13
    • 0003998388 scopus 로고
    • Water solubility of silver oxide is 13 mg and 60 mg in 100 mL of cold and warm water, resp.:. Lide D.R. (Ed), Boca Raton, FL
    • Water solubility of silver oxide is 13 mg and 60 mg in 100 mL of cold and warm water, resp.:. In: Lide D.R. (Ed). Handbook of Chemistry and Physics. 73rd ed. (1993), Boca Raton, FL
    • (1993) Handbook of Chemistry and Physics. 73rd ed.
  • 16
    • 0003590357 scopus 로고
    • For an exceptional review, see:. Patai S., and Rappoport Z. (Eds), John Willey & Sons, Chichester Supplement D, Part 2
    • For an exceptional review, see:. In: Patai S., and Rappoport Z. (Eds). The Chemistry of Halides, Pseudo-halides and Azides (1983), John Willey & Sons, Chichester Supplement D, Part 2
    • (1983) The Chemistry of Halides, Pseudo-halides and Azides


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.