메뉴 건너뛰기




Volumn 69, Issue 14, 2004, Pages 4577-4585

Mechanism of novel consecutive rearrangements of cyclobutene-fused diphenylhomobenzoquinones catalyzed by Lewis acids

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; THERMODYNAMIC STABILITY; TITANIUM COMPOUNDS;

EID: 3142534627     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035830k     Document Type: Article
Times cited : (11)

References (48)
  • 1
    • 3142639232 scopus 로고    scopus 로고
    • Molecular rearrangements
    • Knipe, A. C., Watts, W. F., Eds.; John Wiley & Sons: Chichester; Chapter 15
    • (a) Murray, A. W. Molecular Rearrangements. In Organic Reaction Mechanisms; Knipe, A. C., Watts, W. F., Eds.; John Wiley & Sons: Chichester, 2003; Chapter 15, pp 487-615.
    • (2003) Organic Reaction Mechanisms , pp. 487-615
    • Murray, A.W.1
  • 3
    • 0004052210 scopus 로고
    • Oxford University Press Inc.: New York
    • (c) Harwood; L. M. Polar Rearrangements; Oxford University Press Inc.: New York, 1992.
    • (1992) Polar Rearrangements
    • Harwood, L.M.1
  • 4
    • 3142635204 scopus 로고
    • Rearrangements and fragmentations
    • John Wiley & Sons: New York; Chapter 13
    • (d) Ho., T.-L. Rearrangements and Fragmentations. In Tandem Organic Reactions; John Wiley & Sons: New York, 1992; Chapter 13, pp 361-397.
    • (1992) Tandem Organic Reactions , pp. 361-397
    • Ho, T.-L.1
  • 8
    • 0001310616 scopus 로고
    • Degenerate carbocation rearrangements
    • Gold, V., Bethell, D., Eds.; Academic Press: London
    • (h) Ahlberg, P.; Jonsall, G.; Engdahl, C. Degenerate Carbocation Rearrangements. In Advances in Physical Organic Chemistry; Gold, V., Bethell, D., Eds.; Academic Press: London, 1983; Vol. 19, pp 223-379.
    • (1983) Advances in Physical Organic Chemistry , vol.19 , pp. 223-379
    • Ahlberg, P.1    Jonsall, G.2    Engdahl, C.3
  • 23
    • 3142599316 scopus 로고    scopus 로고
    • note
    • The pseudo-boat conformation can be anticipated by the dihedral angle (θ) of 172.3° for the linkage of O(1)-C(8)-C(14)-C(4) and -178.7° for O(2)-C(12)-C(4)-C(14), respectively; see Figure 1.
  • 24
    • 3142533036 scopus 로고    scopus 로고
    • note
    • This is reflected in the smaller dihedral angle (θ) of 109.2° for the C(15)-C(4)-C(14)-C(8) linkage involving cyclobutene σ-bond as compared to 135.3° for the C(8)-C(14)-C(4)-C(26) linkage involving the quinone methyl substituent; see Figure 1.
  • 25
    • 0004293179 scopus 로고
    • Oxford University Press, Inc.: New York
    • (a) Kirby, A. J. Stereoelectronic Effects; Oxford University Press, Inc.: New York, 1966.
    • (1966) Stereoelectronic Effects
    • Kirby, A.J.1
  • 36
    • 3142609417 scopus 로고    scopus 로고
    • note
    • 4 are rather complicated because of their strong tendency to form the 2:1 complexes and the 1:1 dimeric complexes, satisfying the desire of Ti and Sn for hexacoordination; see ref 18.
  • 37
    • 3142539224 scopus 로고    scopus 로고
    • note
    • The transoid binding may allow the favorable σ*-σ interaction between the coordination σ* bond and the adjacent cyclopropane connecting σ-bond. Such an orbital interaction will intensify the electron demand of the relevant bond, which results in the promotion of the cyclopropane ring cleavage; see ref 7.
  • 44
    • 3142603353 scopus 로고    scopus 로고
    • note
    • Incidentally, the isolated 4bα was easily transformed into the intramolecular [2 + 2] photoadduct on irradiation with a 300 W high-pressure mercury lamp. Details will be described elsewhere.
  • 45
    • 0001693455 scopus 로고
    • 4 is well-known and confirmed in crystal structures of the complexes with ethyl acetate and ethyl anisate. For example, see: (a) Brun, L. Acta Crystallogr. 1966, 20, 739.
    • (1966) Acta Crystallogr. , vol.20 , pp. 739
    • Brun, L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.