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Volumn 77, Issue 20, 2012, Pages 8845-8850

Analogies between synthetic and biosynthetic reactions in which [1,2]-alkyl shifts are combined with other events: Dyotropic, schmidt, and carbocation rearrangements

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCATIONS; COMPUTATIONAL STUDIES;

EID: 84867692133     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301864h     Document Type: Article
Times cited : (52)

References (80)
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    • Leading references on σ-bond methathesis
    • Leading references on σ-bond methathesis: Ziegler, T.; Folga, E.; Berces, A. J. Am. Chem. Soc. 1993, 115, 636-646
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 636-646
    • Ziegler, T.1    Folga, E.2    Berces, A.3
  • 48
    • 84875813513 scopus 로고    scopus 로고
    • Although it was first thought that this dyotropic reaction did not occur under the experimental conditions, the calculations indicated that it should, thus prompting additional experiments. These demonstrated that the predicted product did indeed form but was subsequently hydrolyzed in the presence of adventitious TfOH. The Brønsted acid promoted dyotropic reaction was, in fact, predicted to be a barrierless process.
    • Although it was first thought that this dyotropic reaction did not occur under the experimental conditions, the calculations indicated that it should, thus prompting additional experiments. These demonstrated that the predicted product did indeed form but was subsequently hydrolyzed in the presence of adventitious TfOH. The Brønsted acid promoted dyotropic reaction was, in fact, predicted to be a barrierless process.
  • 50
    • 77951872771 scopus 로고    scopus 로고
    • An unusual dyotropic rearrangement, with two migrating alkyl groups, recently was also predicted using DFT calculations to have a barrier of approximately 100 kcal/mol, consistent with the early predictions of Hoffmann and Williams.(7) See
    • An unusual dyotropic rearrangement, with two migrating alkyl groups, recently was also predicted using DFT calculations to have a barrier of approximately 100 kcal/mol, consistent with the early predictions of Hoffmann and Williams.(7) See: Gryko, D. T.; Rogacki, M. K.; Klajn, J.; Galezowski, M.; Stepien, D. K.; Cyranski, M. K. Org. Lett. 2010, 12, 2020-2023
    • (2010) Org. Lett. , vol.12 , pp. 2020-2023
    • Gryko, D.T.1    Rogacki, M.K.2    Klajn, J.3    Galezowski, M.4    Stepien, D.K.5    Cyranski, M.K.6
  • 54
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    • For a related example, see ref 25
    • Hong, Y. J.; Tantillo, D. J. J. Am. Chem. Soc. 2009, 131, 7999-8015 For a related example, see ref 25
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 7999-8015
    • Hong, Y.J.1    Tantillo, D.J.2
  • 60
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    • (1924) Ber. , vol.57 , pp. 704-723
    • Schmidt, K.F.1
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    • Curtius, T. Ber. 1890, 23, 3023
    • (1890) Ber. , vol.23 , pp. 3023
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  • 74
    • 80053009359 scopus 로고
    • Hofmann, A. W. Ber. 1881, 14, 2725
    • (1881) Ber. , vol.14 , pp. 2725
    • Hofmann, A.W.1
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    • Beckmann, E. Ber. 1886, 19, 988-993
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    • Beckmann, E.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.