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Volumn , Issue 16, 2009, Pages 2687-2694

Microwave-assisted competing domino processes in the octaline diol series

Author keywords

Diols; Domino reactions; Lead; Microwave chemistry

Indexed keywords


EID: 66249116652     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900242     Document Type: Article
Times cited : (11)

References (37)
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    • For routes to gain synthetic entry into cycloheptanes as synthetic goal compounds, see
    • For routes to gain synthetic entry into cycloheptanes as synthetic goal compounds, see:
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    • P. A. Wender, H. Rieck, M. Fuji, J. Am. Chem. Soc. 1998,120, 10976-10977;
    • e) P. A. Wender, H. Rieck, M. Fuji, J. Am. Chem. Soc. 1998,120, 10976-10977;
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    • For reviews on the use of microwaves in organic synthesis, see: a
    • For reviews on the use of microwaves in organic synthesis, see: a) A. de la Hoz, A. Diaz-Ortis, A. Moreno, F. Langa, Eur. J. Org. Chem. 2000, 3659-3673;
    • (2000) Eur. J. Org. Chem , pp. 3659-3673
    • de la Hoz, A.1    Diaz-Ortis, A.2    Moreno, A.3    Langa, F.4
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    • Eds, M. Shibasaki, J. F. Stod-dart, F. Vogtle, Wiley-VCH, Weinheim
    • d) L. F. Tietze, F. Haunert in Stimulating Concepts in Chemistry (Eds.: M. Shibasaki, J. F. Stod-dart, F. Vogtle), Wiley-VCH, Weinheim, 2000, pp. 39-64;
    • (2000) Stimulating Concepts in Chemistry , pp. 39-64
    • Tietze, L.F.1    Haunert, F.2
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    • For comparison, in the hydrindene diol series, these results were unchanged by substituting toluene for the more polar solvent acetic acid
    • For comparison, in the hydrindene diol series, these results were unchanged by substituting toluene for the more polar solvent acetic acid.
  • 26
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    • 2 could be used, as the domino promoters.
    • 2 could be used, as the domino promoters.
  • 27
    • 66249103394 scopus 로고    scopus 로고
    • 2 and AcOH. For articles dealing with specific aspects of organolead chemistry, see: a) R. Criegee in Oxidation In Organic Chemistry (Eds.: K. B. Wiberg), Academic Press, New York, 1965, part A, pp. 277-366;
    • 2 and AcOH. For articles dealing with specific aspects of organolead chemistry, see: a) R. Criegee in Oxidation In Organic Chemistry (Eds.: K. B. Wiberg), Academic Press, New York, 1965, part A, pp. 277-366;
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    • Eds, W. H. Trahanovsky, Academic Press, London, ch. 1;
    • b) G. M. Rubottom in Oxidation In Organic Chemistry (Eds.: W. H. Trahanovsky), Academic Press, London, 1982, vol. D, ch. 1;
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    • In the absence of microwave irradiation, the use of water as solvent gives a messy reaction mixture containing 2 and. 6, along with starting diols and unidentified, products
    • In the absence of microwave irradiation, the use of water as solvent gives a messy reaction mixture containing 2 and. 6, along with starting diols and unidentified, products.
  • 32
    • 66249128679 scopus 로고    scopus 로고
    • All reactions were performed, on racemic series; only one antipode is represented. The stereochemistry of the diol had no effect on the reaction, as demonstrated by control experiments where substrates with cis diols performed identically to substrates with trans diols. Ultrasonic conditions were probed for their likely helpful advantages, but to no benefit.
    • All reactions were performed, on racemic series; only one antipode is represented. The stereochemistry of the diol had no effect on the reaction, as demonstrated by control experiments where substrates with cis diols performed identically to substrates with trans diols. Ultrasonic conditions were probed for their likely helpful advantages, but to no benefit.
  • 34
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    • The stereochemistry at the secondary hydroxy groups at C2 and C3 is not important, as it is destroyed in the generation of [4π+2π] template i (Figure 1). 4
    • The stereochemistry at the secondary hydroxy groups at C2 and C3 is not important, as it is destroyed in the generation of [4π+2π] template i (Figure 1). 4
  • 35
    • 66249137854 scopus 로고    scopus 로고
    • The low yields obtained in these reactions could be explained by the fact that the likely domino products from the epimeric contribution are sensitive to the workup and chromatographic conditions used
    • The low yields obtained in these reactions could be explained by the fact that the likely domino products from the epimeric contribution are sensitive to the workup and chromatographic conditions used.
  • 36
    • 66249126010 scopus 로고    scopus 로고
    • That clearly means that oxidative cleavage under microwave irradiation is faster than hydrolysis of the reagent
    • That clearly means that oxidative cleavage under microwave irradiation is faster than hydrolysis of the reagent.
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    • For entropie and. enthalpic factors during the formation of medium-sized rings, see
    • For entropie and. enthalpic factors during the formation of medium-sized rings, see: G. Illuminati, L. Mandolini, Ace. Chem. Res. 1981, 14, 95-101.
    • (1981) Ace. Chem. Res , vol.14 , pp. 95-101
    • Illuminati, G.1    Mandolini, L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.