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Volumn 122, Issue 25, 2000, Pages 6078-6092

Origins of the loss of concertedness in pericyclic reactions: Theoretical prediction and direct observation of stepwise mechanisms in [3 + 2] thermal cycloadditions

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PREDICTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034725364     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9945360     Document Type: Article
Times cited : (118)

References (114)
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    • Vedejs, E.1
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    • For recent examples, see: (a) Barr, D. A.; Dorrity, M. J.; Grigg, R.; Malone, J. F.; Montgomery, J.; Rajviroongit, S.; Stevenson, P. Tetrahedron Lett. 1990, 31, 6569. (b) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. (c) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431.
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  • 20
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    • For recent examples, see: (a) Barr, D. A.; Dorrity, M. J.; Grigg, R.; Malone, J. F.; Montgomery, J.; Rajviroongit, S.; Stevenson, P. Tetrahedron Lett. 1990, 31, 6569. (b) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. (c) Grigg, R.; Montgomery, J.; Somasunderam, A. Tetrahedron 1992, 48, 10431.
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    • and references therein
    • As one reviewer has indicated, this is an approximation of the solvation energy. Similarly, the ε function is a very crude estimate of solvent polarity. See ref 46 for more detailed treatment of this problem. See also: Huisgen, R. Pure Appl. Chem. 1981, 53, 171 and references therein.
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    • (b) Barrett, A. G. M.; Grabosky, G. G. Chem. Rev. 1986, 86, 751. For [3 + 2] cycloadditions between azomethine ylides and nitro-olefins see: Pak, C. S.; Nyerges, M. Synlett 1999, 1271 and references therein.
    • (1986) Chem. Rev. , vol.86 , pp. 751
    • Barrett, A.G.M.1    Grabosky, G.G.2
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    • and references therein
    • (b) Barrett, A. G. M.; Grabosky, G. G. Chem. Rev. 1986, 86, 751. For [3 + 2] cycloadditions between azomethine ylides and nitro-olefins see: Pak, C. S.; Nyerges, M. Synlett 1999, 1271 and references therein.
    • (1999) Synlett , vol.1271
    • Pak, C.S.1    Nyerges, M.2
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    • note
    • -1, T = 173(1) K, Mo Kα radiation (λ = 0.71069 Å), Rigaku AFC5R diffractometer, ω/2θ scans. Refinement on F gave R = 0.0399, wR = 0.0359, GOF = 1.767 using 294 refined parameters and 2594 observed reflections with I > 2σ(I) from the 3333 collected (3219 unique) with 2θ < 55°. The structure was solved by direct methods and all non-hydrogen atoms were refined anisotropically.
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    • note
    • -1, T = 173(1) K, Mo Kα radiation (λ = 0.71069 Å), Rigaku AFC5R diffractometer, ω/2θ scans. Refinement on F gave R = 0.0589, wR = 0.0463, GOF = 1.686 using 203 refined parameters and 1806 observed reflections with I > 2σ(I) from the 3838 collected (3506 unique) with 2θ < 55°. The structure was solved by direct methods and all non-hydrogen atoms were refined anisotropically.
  • 95
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    • (c) Eckell, A.; George, M. V.; Huisgen, R.; Kende, A. S. Chem. Ber. 1977, 110, 578. See also: Böhm, T.; Elender, K.; Riebel, P.; Troll, T.; Weber, A.; Sauer, J. Tetrahedron 1999, 55, 9515.
    • (1977) Chem. Ber. , vol.110 , pp. 578
    • Eckell, A.1    George, M.V.2    Huisgen, R.3    Kende, A.S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.