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Volumn 45, Issue 35, 2006, Pages 5803-5807

Three groups good, four groups bad? Atropisomerism in ortho-substituted diaryl ethers

Author keywords

Atropisomerism; Diaryl ethers; NMR spectroscopy; Rotational barriers; Stereochemistry

Indexed keywords

CYCLIC VOLTAMMETRY; ISOMERIZATION; STEREOCHEMISTRY; STRUCTURE (COMPOSITION); SUBSTITUTION REACTIONS; THERMAL EFFECTS;

EID: 33748545334     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601866     Document Type: Article
Times cited : (66)

References (46)
  • 26
    • 33748536693 scopus 로고    scopus 로고
    • note
    • c value were simulated by using gNMR software (Adept Scientific).
  • 27
    • 33748573269 scopus 로고    scopus 로고
    • note
    • The half-lives are for the approach to the equilibrium mixture, not half-lives for bond rotation. The bond rotation monitored in 6c, 7c, and 8c does not in fact lead to interconversion of stereoisomers, but the half-life value is calculated in the same way for consistency.
  • 34
    • 33748548362 scopus 로고    scopus 로고
    • note
    • This estimation is made on the assumption that at least one pair of diastereotopic or more or less equally populated diastereoisomeric peaks would have a peak separation of > 0.1 ppm at the slow exchange limit.
  • 35
    • 33748535738 scopus 로고    scopus 로고
    • note
    • Substituents attached to the symmetrical ring may show coalescences at higher temperatures, which is indicative of much higher barriers, but these must be barriers to nonconcerted bond rotations; a full discussion will follow in a later report.
  • 40
    • 33748557211 scopus 로고    scopus 로고
    • note
    • Ground-state destabilization of tetra-ortho-substituted relative to tri-ortho-substituted diaryl ethers may also play a role in lowering the barrier, but the results presented in Table 1, entries 22-25 suggest that it is not an important one.
  • 41
    • 0000900061 scopus 로고    scopus 로고
    • For a discussion of geared rotation in related compounds, see: J. Clayden, J. H. Pink, Angew. Chem. 1998, 110, 2040;
    • (1998) Angew. Chem. , vol.110 , pp. 2040
    • Clayden, J.1    Pink, J.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.