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Volumn 65, Issue 42, 2009, Pages 8733-8737

AlCl3-NaI(NaBr)-t-BuOH: mild, chemo- and stereoselective reagents for hydrohalogenation of propiolic derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ACETONITRILE; ACRYLIC ACID DERIVATIVE; ALUMINUM CHLORIDE; AMIDE; DICHLOROMETHANE; IODINE DERIVATIVE; PROPYLENE; SODIUM BROMIDE; TERT BUTYL ALCOHOL;

EID: 70049109806     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.032     Document Type: Article
Times cited : (7)

References (26)
  • 17
    • 70049101710 scopus 로고    scopus 로고
    • note
    • The mechanism, involves conjugate addition of halide anion to the activated substrate. The intermediate allenoate is protonated at the less hindered face of the double bond, i.e., the opposite side relative to the halogen atom. This explains the selectivity observed in favour of the (Z)-isomer.
  • 20
    • 70049102089 scopus 로고    scopus 로고
    • note
    • For sake of comparison all reactions were analyzed after 18 h. However, monitoring hydroiodination of 1a proved that the reaction was completed within 4 h. The similarity of isolated yields showed that no further degradation occurred.
  • 21
    • 70049113755 scopus 로고    scopus 로고
    • note
    • In this case isomerization into the most stable (E)-isomer occurred, see: Ref. 4b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.