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Volumn 127, Issue 27, 2005, Pages 9939-9945

Utilization of an oxonia-Cope rearrangement as a mechanistic probe for Prins cyclizations

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUNDS; POSITIVE IONS; STRUCTURE (COMPOSITION); SUBSTITUTION REACTIONS;

EID: 22144498082     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0518326     Document Type: Article
Times cited : (104)

References (44)
  • 1
    • 2642675659 scopus 로고
    • For reviews on the Prins cyclization, see: (a) Arundale, E.; Mikeska, L. A. Chem. Rev. 1952, 52, 505-555.
    • (1952) Chem. Rev. , vol.52 , pp. 505-555
    • Arundale, E.1    Mikeska, L.A.2
  • 3
    • 0001290261 scopus 로고
    • Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York
    • (c) Snider, B. B. In The Prins Reaction and Carbonyl Ene Reactions; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 2. pp 527-561.
    • (1991) The Prins Reaction and Carbonyl Ene Reactions , vol.2 , pp. 527-561
    • Snider, B.B.1
  • 5
    • 3242676775 scopus 로고    scopus 로고
    • For recent work on the Prins cyclization. see: (a) Yadav, K. V.; Kumar, N. V. J. Am. Chem. Soc. 2004, 126, 8652-8653.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 8652-8653
    • Yadav, K.V.1    Kumar, N.V.2
  • 26
    • 4344610661 scopus 로고    scopus 로고
    • For reviews on the Claisen and Cope rearrangements, see: (a) Martin Castro, A. M. Chem. Rev. 2004, 104, 2939-3002.
    • (2004) Chem. Rev. , vol.104 , pp. 2939-3002
    • Martin Castro, A.M.1
  • 32
    • 0003467672 scopus 로고
    • John Wiley & Sons: New York
    • March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992; p 782. "Those reactions are favored which involve the least change in atomic position and electronic configuration."
    • (1992) Advanced Organic Chemistry, 4th Ed. , pp. 782
    • March, J.1
  • 40
    • 32744461058 scopus 로고    scopus 로고
    • note
    • A reviewer suggested a crossover experiment utilizing tetrabutylammonium chloride as a competitive nucleophile. We found that generation of a bromoether from acetoxy ether 25 at -60 °C followed by addition of tetrabutylammonium chloride and warming to 0 °C led to axial bromotetrahydropyran 27 in 83% ee. No chlorotetrahydropyrans were observed in the crude reaction mixture. This result is consistent with an ion-pairing argument in which recombination of a bromide anion from inside a solvent cage is faster than incorporation of a chloride anion from outside a solvent cage.
  • 41
    • 0029968191 scopus 로고    scopus 로고
    • Carbocations which are not highly stabilized are known to be quenched at a diffusional rate: (a) McCelland, R. A. Tetrahedron 1996, 52, 6823.
    • (1996) Tetrahedron , vol.52 , pp. 6823
    • McCelland, R.A.1
  • 43
    • 32744464183 scopus 로고    scopus 로고
    • note
    • 20 Minima were characterized by their vibrational frequencies. Reported energies include unsealed zero-point corrections.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.