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Volumn 55, Issue 45, 1999, Pages 12939-12956

Synthesis, structure and AM1 conformational study of [3]paracyclo[3](1,3)indolophane, a novel chiral cyclophane

Author keywords

Cyclophanes; Indoles; X ray crystal structures

Indexed keywords

INDOLE; PARACYCLOPHANE DERIVATIVE;

EID: 0033527804     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00792-9     Document Type: Article
Times cited : (23)

References (49)
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    • note
    • There are many naturally occurring indole alkaloids as well as non-natural indole-based compounds that feature aliphatic rings fused to the indole nucleus. Although such compounds technically fit the definition of a cyclophane, we consider these to be outside the scope of the current investigation. This blanket omission is directly analogous to that of many orthocyclophanes from the benzenoid family. For example [2]-, [3]-, [4]- and [5]orthocyclophane are not normally viewed as cyclophanes, but rather as benzocyclobutene, indan, 1,2,3,4-tetrahydronaphthalene and benzocycloheptene, respectively. This is not to say, however, that the ortho mode of bridge attachment necessarily disqualifies a compound from being a cyclophane.
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    • The terms "chair" and "boat" are used in a sense analogous to that for [3.3]metacyclophanes, [3.3]metaparacyclophanes and [3.3]orthometacyclophanes. See for example: refs 1, 6f and
    • The terms "chair" and "boat" are used in a sense analogous to that for [3.3]metacyclophanes, [3.3]metaparacyclophanes and [3.3]orthometacyclophanes. See for example: refs 1, 6f and Anker, W.; Bushnell, G.; Mitchell, R. H. Can. J. Chem. 1979, 57, 3080-3087.
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    • Strictly speaking, the Gutowsky-Holm equation applies only to equally populated singlets, in which the signal width is small relative to Δν. As such, the free energy of activation calculated here may be overstated. See Mitchell, R. H. in ref 1d, Vol. 1, Ch. 4, p. 265, and references cited therein
    • Gutowsky, H. S.; Holm, C. H. J. Chem. Phys. 1956, 25, 1228-1234. Strictly speaking, the Gutowsky-Holm equation applies only to equally populated singlets, in which the signal width is small relative to Δν. As such, the free energy of activation calculated here may be overstated. See Mitchell, R. H. in ref 1d, Vol. 1, Ch. 4, p. 265, and references cited therein.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.