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Volumn 11, Issue 14, 2009, Pages 3056-3058

Controllable selective functionalization of a cavitand via solid state photolysis of an encapsulated phenyl azide

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EID: 67650559347     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901122h     Document Type: Article
Times cited : (12)

References (30)
  • 1
    • 13644254551 scopus 로고    scopus 로고
    • and citations therein
    • (i) warmutn, K.; Makowiec, s. j. Am. Chem. Soc. 2005, 127, 1084 and citations therein.
    • (2005) Am. Chem. Soc , vol.127 , pp. 1084
    • warmutn, K.1    Makowiec2
  • 2
    • 67650542703 scopus 로고    scopus 로고
    • Platz, M. S. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Jr.; Wiley: Hoboken, NJ, 2004; p 522.
    • (b) Platz, M. S. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Jr.; Wiley: Hoboken, NJ, 2004; p 522.
  • 12
    • 67650560311 scopus 로고    scopus 로고
    • We ascertained that phenyl azide (1) forms a 1:1 complex with cavitand 2 with an association constant of K = 60 M-1 in acetone-d6.
    • We ascertained that phenyl azide (1) forms a 1:1 complex with cavitand 2 with an association constant of K = 60 M-1 in acetone-d6.
  • 16
    • 67650557426 scopus 로고    scopus 로고
    • Enlarged images of the X-ray structure and the crystal packing are given in the Supporting Information
    • Enlarged images of the X-ray structure and the crystal packing are given in the Supporting Information.
  • 19
    • 67650539932 scopus 로고    scopus 로고
    • All yields reported in this paper were ascertained by HPLC measurements of the crude product mixtures nitrobenzene as internal standard, Isolated yields are listed in the Supporting Information
    • All yields reported in this paper were ascertained by HPLC measurements of the crude product mixtures (nitrobenzene as internal standard). Isolated yields are listed in the Supporting Information.
  • 20
    • 67650521034 scopus 로고    scopus 로고
    • Again, the DSC analysis provides evidence for a two-step dissociation process. Two-thirds of 1 are released at 145 °C with ΔH = 16.6 kcal/mol. This process is significantly more endothermic than the dissociation of the 1:1 complex before heating the probe. Most probably, the thermal treatment leads to a thermodynamically more favorable modification of the crystal lattice. The remaining phenyl azide (1) is released at 169 °C (ΔH = 2.2 kcal/mol).
    • Again, the DSC analysis provides evidence for a two-step dissociation process. Two-thirds of 1 are released at 145 °C with ΔH = 16.6 kcal/mol. This process is significantly more endothermic than the dissociation of the 1:1 complex before heating the probe. Most probably, the thermal treatment leads to a thermodynamically more favorable modification of the crystal lattice. The remaining phenyl azide (1) is released at 169 °C (ΔH = 2.2 kcal/mol).
  • 23
    • 67650542702 scopus 로고    scopus 로고
    • 7(C,H) = 152, 163 and 155, 163 Hz for the aziridine rings in 5 and 7, respectively. For further details, see the Supporting Information.
    • 7(C,H) = 152, 163 and 155, 163 Hz for the aziridine rings in 5 and 7, respectively. For further details, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.