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Volumn 11, Issue 3, 2009, Pages 507-510

Preparation of bicyclic 1,2,4-trioxanes from γ,δ-unsaturated ketones

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIOXANE; 1,2,4-TRIOXANE; ALKENE; HETEROCYCLIC COMPOUND; HYDROGEN PEROXIDE; KETONE;

EID: 60849089373     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8022853     Document Type: Article
Times cited : (33)

References (50)
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    • (c) Wu, Y. Ace. Chem. Res. 2002, 35, 255-259.
    • (2002) Ace. Chem. Res , vol.35 , pp. 255-259
    • Wu, Y.1
  • 5
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    • (a) Klayman, D. L. Science 1985, 228, 1049-1055.
    • (1985) Science , vol.228 , pp. 1049-1055
    • Klayman, D.L.1
  • 25
    • 0000977859 scopus 로고
    • and references cited therein
    • Kharasch, M. S.; Sosnovsky, G. J. Org. Chem. 1958, 23, 1322-1326, and references cited therein.
    • (1958) J. Org. Chem , vol.23 , pp. 1322-1326
    • Kharasch, M.S.1    Sosnovsky, G.2
  • 30
    • 62149116114 scopus 로고    scopus 로고
    • Peroxide oligomers are potentially hazardous and explosive: Zabicky, J. The Chemistry of Peroxides; Rappoport, Z., Ed.; Wiley: Chichester, UK, 2006; 2, Chapter 7, pp 597-774. No difficulties were encountered in the handling or purification of these compounds on small scale. Details are provided in the Supporting Information.
    • Peroxide oligomers are potentially hazardous and explosive: Zabicky, J. The Chemistry of Peroxides; Rappoport, Z., Ed.; Wiley: Chichester, UK, 2006; Vol. 2, Chapter 7, pp 597-774. No difficulties were encountered in the handling or purification of these compounds on small scale. Details are provided in the Supporting Information.
  • 31
    • 0032818397 scopus 로고    scopus 로고
    • Treatment of carbonyl compounds with acidic hydrogen peroxide or its derivatives can yield peroxide oligomers and Baeyer-Villiger oxidation products: Renz, M, Meunier, B, Chem. 1999, 737-750
    • Treatment of carbonyl compounds with acidic hydrogen peroxide or its derivatives can yield peroxide oligomers and Baeyer-Villiger oxidation products: Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 737-750.
  • 32
  • 36
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    • Details are provided in the Supporting Information
    • Details are provided in the Supporting Information.
  • 40
    • 33947484828 scopus 로고    scopus 로고
    • Cyclization of the 1,2-dibromo alkane in a related system has been reported: (a) Holum, J. R.; Jorenby, D.; Mattison, P. J. Org. Chem. 1964, 29, 769-776.
    • Cyclization of the 1,2-dibromo alkane in a related system has been reported: (a) Holum, J. R.; Jorenby, D.; Mattison, P. J. Org. Chem. 1964, 29, 769-776.
  • 47
    • 62149150722 scopus 로고    scopus 로고
    • Reaction conditions have not been optimized
    • Reaction conditions have not been optimized.
  • 49
    • 62149109407 scopus 로고    scopus 로고
    • In other experiments, 1,2-disubstituted alkenes without the phenyl group did not form the desired 1,2,4-trioxanes. It appears that the additional stability of the proposed carbocationic intermediate 33 (Table 3) conferred by the phenyl substituent allowed the product to form from a disubstituted alkene
    • In other experiments, 1,2-disubstituted alkenes without the phenyl group did not form the desired 1,2,4-trioxanes. It appears that the additional stability of the proposed carbocationic intermediate 33 (Table 3) conferred by the phenyl substituent allowed the product to form from a disubstituted alkene.
  • 50
    • 62149119650 scopus 로고    scopus 로고
    • Loss of stereochemistry was also observed in trisubstituted alkene substrates (Table 2, entry 6).
    • Loss of stereochemistry was also observed in trisubstituted alkene substrates (Table 2, entry 6).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.