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Volumn 12, Issue 15, 2010, Pages 3398-3401

Strained to the limit: When a cyclobutyl moiety becomes a thermodynamic sink in a protolytic ring-opening of photogenerated oxetanes

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; 2-CYCLOHEXEN-1-ONE; CHLOROHYDRIN DERIVATIVE; CYCLOHEXANONE DERIVATIVE; FUSED HETEROCYCLIC RINGS; POLYCYCLIC AROMATIC HYDROCARBON;

EID: 77955165928     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101297b     Document Type: Article
Times cited : (17)

References (20)
  • 12
    • 77955170020 scopus 로고    scopus 로고
    • Synthesis of D.-A. adducts 1-4, 9, 12 is described in the literature
    • Synthesis of D.-A. adducts 1-4, 9, 12 is described in the literature
  • 16
    • 77955144459 scopus 로고    scopus 로고
    • 1/2 ≈ 7 Hz. We also were able to accurately calculate their NMR spectra-see SI. Attempts to further purify reaction mixtures by column chromatography were mainly unsuccessful, as the strained polycyclic oxetanes 5-8 are not stable on silica gel, producing varying amounts of rearranged products
    • 1/2 ≈ 7 Hz. We also were able to accurately calculate their NMR spectra-see SI. Attempts to further purify reaction mixtures by column chromatography were mainly unsuccessful, as the strained polycyclic oxetanes 5-8 are not stable on silica gel, producing varying amounts of rearranged products.
  • 18
    • 77955154782 scopus 로고    scopus 로고
    • 2, 1-3 mol equiv of HCl (4.0 M solution in dioxane) was added. The resulting mixture was stirred at ambient temperature for 24 h, the solvent was removed in vacuum, and the products were purified by chromatography on a silica gel column using hexane-ethyl acetate (or hexane-ethanol) as eluent
    • 2, 1-3 mol equiv of HCl (4.0 M solution in dioxane) was added. The resulting mixture was stirred at ambient temperature for 24 h, the solvent was removed in vacuum, and the products were purified by chromatography on a silica gel column using hexane-ethyl acetate (or hexane-ethanol) as eluent.
  • 20
    • 77955124852 scopus 로고    scopus 로고
    • Notice that the same outcome can be achieved with an alternating sequence of (1,3-hydride)-(1,2-alkyl)-(1,3-hydride) shifts
    • Notice that the same outcome can be achieved with an alternating sequence of (1,3-hydride)-(1,2-alkyl)-(1,3-hydride) shifts.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.