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Volumn 53, Issue 27, 1997, Pages 9023-9042

On the mechanism of the intramolecular samarium barbier reaction. Probes for formation of radical and organosamarium intermediates

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; ORGANOMETALLIC COMPOUND; RADICAL; SAMARIUM;

EID: 0030962154     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00608-X     Document Type: Article
Times cited : (71)

References (56)
  • 30
    • 0343029297 scopus 로고    scopus 로고
    • note
    • We define the terms "Grignard" and "Barbier" based on experimental procedures (eq 1) not mechanisms. In an intramolecular reaction, the halide and ketone are attached, so only the Barbier procedure is possible.
  • 33
  • 36
    • 0343465103 scopus 로고    scopus 로고
    • A similar experiment was performed by Molander and McKie in a bridged system, with similar results (ref. 9b)
    • A similar experiment was performed by Molander and McKie in a bridged system, with similar results (ref. 9b).
  • 41
    • 0342595178 scopus 로고    scopus 로고
    • This assumes that ketyl opening is not reversible
    • This assumes that ketyl opening is not reversible.
  • 42
    • 0343029293 scopus 로고    scopus 로고
    • note
    • The postulate of intramolecular electron transfer suggests that iodoketones might to more reactive than alkyl iodides. The following competition experiment is constant with this suggestion. (Formula Presented)
  • 46
    • 0343029292 scopus 로고    scopus 로고
    • note
    • N2-based mechanisms with ketyls, but this type of nucleophilic substitution is supposed to be strongly disfavored with respect to electron transfer. See reference 16.
  • 47
    • 0342595177 scopus 로고    scopus 로고
    • 2
    • 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.