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Volumn 61, Issue 24, 1996, Pages 8681-8684

Oxyfunctionalization of non-natural targets by dioxiranes. 2. Selective bridgehead dihydroxylation of fenestrindane

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EID: 0000467349     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961316l     Document Type: Article
Times cited : (27)

References (51)
  • 3
    • 3643137718 scopus 로고    scopus 로고
    • in press
    • For accounts on centropolyindane chemistry, see: (a) Kuck, D. Synlett 1996, in press. (b) Kuck, D. In Quasicrystals, Networks, and Molecules of Fivefold Symmetry; Hargittai, I., Ed.; VCH: New York, 1990; Chapter 19.
    • (1996) Synlett
    • Kuck, D.1
  • 4
    • 3643055362 scopus 로고
    • Hargittai, I., Ed.; VCH: New York, Chapter 19
    • For accounts on centropolyindane chemistry, see: (a) Kuck, D. Synlett 1996, in press. (b) Kuck, D. In Quasicrystals, Networks, and Molecules of Fivefold Symmetry; Hargittai, I., Ed.; VCH: New York, 1990; Chapter 19.
    • (1990) Quasicrystals, Networks, and Molecules of Fivefold Symmetry
    • Kuck, D.1
  • 12
    • 84948351019 scopus 로고
    • See references to the pertinent articles quoted therein
    • For recent reviews on dioxirane reactivity, see: (a) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811. See references to the pertinent articles quoted therein.
    • (1995) Pure Appl. Chem. , vol.67 , pp. 811
    • Curci, R.1    Dinoi, A.2    Rubino, M.F.3
  • 13
    • 0001218439 scopus 로고
    • Ando, W., Ed.; Wiley: New York, Chapter 4, See references therein
    • (b) Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; Chapter 4, pp 195-219. See references therein.
    • (1992) Organic Peroxides , pp. 195-219
    • Adam, W.1    Hadjiarapoglou, L.P.2    Curci, R.3    Mello, R.4
  • 24
    • 84989487596 scopus 로고
    • (a) Kuck, D. Chem. Ber. 1994, 127, 409.
    • (1994) Chem. Ber. , vol.127 , pp. 409
    • Kuck, D.1
  • 27
    • 3643072069 scopus 로고    scopus 로고
    • note
    • [5.5.5.5]Fenestranes containing more than four double bonds in the fenestrane core have been discussed in the literature (ref 16) in the context of the planar-tetracoordinate-carbon problem (ref 17).
  • 36
    • 0041327187 scopus 로고
    • Kagan, H. B., Ed.; Thieme: Stuttgart, Germany
    • For a general discussion of stereospecific water elimination processes in gaseous radical cations of alcohols, see: Mandelbaum, A. In Stereochemistry; Kagan, H. B., Ed.; Thieme: Stuttgart, Germany, 1977; Vol. 1, pp 153 ff.
    • (1977) Stereochemistry , vol.1
    • Mandelbaum, A.1
  • 37
    • 85087249289 scopus 로고    scopus 로고
    • note
    • •+) ca. 0.5 (ref 4b).
  • 38
    • 34547165504 scopus 로고
    • 4 molecular symmetry on the NMR time scale. Clearly, the presence of bulky bromine atoms at the bridgehead positions effectively restrains conformational equilibration of the [5.5.5.5]fenestrane skeleton. (See, e.g.: Kuck, D.; Schuster, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 1192.)
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.27 , pp. 1192
    • Kuck, D.1    Schuster, A.2


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