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Volumn 3, Issue 4, 2001, Pages 627-629

Conclusive evidence of the trapping of primary ozonides

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BICYCLO COMPOUND; KETONE; OZONE;

EID: 0035932051     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010005g     Document Type: Article
Times cited : (28)

References (35)
  • 1
    • 0042938853 scopus 로고    scopus 로고
    • note
    • 2000-2001 American Chemical Society Division of Organic Chemistry Graduate Fellow, sponsored by DuPont Pharmaceuticals, Inc.
  • 2
  • 4
    • 0000906140 scopus 로고
    • (b) Criegee, R. Angew. Chem. 1975, 87, 765-772; Angew. Chem., Int. Ed. Engl. 1975, 14, 745-752.
    • (1975) Angew. Chem. , vol.87 , pp. 765-772
    • Criegee, R.1
  • 5
    • 84982344767 scopus 로고
    • (b) Criegee, R. Angew. Chem. 1975, 87, 765-772; Angew. Chem., Int. Ed. Engl. 1975, 14, 745-752.
    • (1975) Angew. Chem., Int. Ed. Engl. , vol.14 , pp. 745-752
  • 13
    • 84972910099 scopus 로고
    • (a) Grob, C. A.; Schiess, P. W. Angew. Chem. 1967, 79, 1-15; Angew. Chem., Int. Ed. Engl. 1967, 6, 1-15.
    • (1967) Angew. Chem. , vol.79 , pp. 1-15
    • Grob, C.A.1    Schiess, P.W.2
  • 14
    • 84972910099 scopus 로고
    • (a) Grob, C. A.; Schiess, P. W. Angew. Chem. 1967, 79, 1-15; Angew. Chem., Int. Ed. Engl. 1967, 6, 1-15.
    • (1967) Angew. Chem., Int. Ed. Engl. , vol.6 , pp. 1-15
  • 15
    • 0001136403 scopus 로고
    • (b) Grob, C. A. Angew. Chem. 1969, 81, 543-554; Angew. Chem., Int. Ed. Engl. 1969, 8, 535-546.
    • (1969) Angew. Chem. , vol.81 , pp. 543-554
    • Grob, C.A.1
  • 16
    • 84981784630 scopus 로고
    • (b) Grob, C. A. Angew. Chem. 1969, 81, 543-554; Angew. Chem., Int. Ed. Engl. 1969, 8, 535-546.
    • (1969) Angew. Chem., Int. Ed. Engl. , vol.8 , pp. 535-546
  • 21
  • 22
    • 0003391908 scopus 로고
    • Trahanovsky, W., Ed.; Academic Press: New York
    • (b) Bailey, P. S. Ozonation in Organic Chemistry; Trahanovsky, W., Ed.; Academic Press: New York, 1978; Vol. 1.
    • (1978) Ozonation in Organic Chemistry , vol.1
    • Bailey, P.S.1
  • 32
    • 0042908644 scopus 로고    scopus 로고
    • note
    • The rest of the material (50%) is the hydroxycyclobutanone 3.
  • 33
    • 0000221391 scopus 로고
    • Prepared by isomerization of the tert-butyldimethylsilyl ether of the E-isomer with iodine and light (to give a 4:3 E to Z ratio) followed by desilylation and separation. It is interesting that Wittig olefination of the corresponding cyclobutanone (prepared from the silyl enol ether of 2-methylcyclopentanone by addition of ethyl propiolate, conversion of the ester to the aldehyde, Baeyer-Villiger oxidation, and hydrolysis) gave only the E-isomer of the alkene, even at high temperatures, in contrast to the work of Still. Sreekumar, C.; Darst, K. P.; Still, W. C. J. Org. Chem. 1980, 45, 4260.
    • (1980) J. Org. Chem. , vol.45 , pp. 4260
    • Sreekumar, C.1    Darst, K.P.2    Still, W.C.3
  • 34
    • 0042908643 scopus 로고
    • It is interesting to note that the hydroxycyclobutanone 3 exists in solution as an equilibrium mixture of 3 and the hydroxyketone 21 in a 2:1 ratio, (a) Harding, K. E.; Trotter, J. W.; May, L. M. J. Org. Chem. 1977, 42, 2715-2719.
    • (1977) J. Org. Chem. , vol.42 , pp. 2715-2719
    • Harding, K.E.1    Trotter, J.W.2    May, L.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.