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Volumn 70, Issue 9, 1997, Pages 2039-2049

Radical Cyclization of Allyl 2-Iodophenyl Ether, N,N-Diallyl-2-iodoaniline, and 2-Iodoethanal Acetal by Means of Trialkylmanganate(II)

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EID: 0000514081     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.2039     Document Type: Article
Times cited : (40)

References (67)
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    • ed by B. M. Trost and I. Fleming, Pergamon Press, New York, Chap. 1.4
    • c) B. H. Lipshutz, in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, New York (1991), Vol. 1, Chap. 1.4, p. 107;
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    • J. Iqbal, B. Bhatia, and N. K. Nayyar, Chem. Rev., 94, 519 (1994); Palladium-catalyzed cyclization: R. C. Larock and D. E. Stinn, Tetrahedron Lett., 29, 4687 (1988); R. C. Larock and S. Babu, Tetrahedron Lett., 28, 5291 (1987); R. C. Larock and D. E. Stinn, Tetrahedron Lett., 30, 2767 (1989);
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    • J. Iqbal, B. Bhatia, and N. K. Nayyar, Chem. Rev., 94, 519 (1994); Palladium-catalyzed cyclization: R. C. Larock and D. E. Stinn, Tetrahedron Lett., 29, 4687 (1988); R. C. Larock and S. Babu, Tetrahedron Lett., 28, 5291 (1987); R. C. Larock and D. E. Stinn, Tetrahedron Lett., 30, 2767 (1989);
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4687
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    • J. Iqbal, B. Bhatia, and N. K. Nayyar, Chem. Rev., 94, 519 (1994); Palladium-catalyzed cyclization: R. C. Larock and D. E. Stinn, Tetrahedron Lett., 29, 4687 (1988); R. C. Larock and S. Babu, Tetrahedron Lett., 28, 5291 (1987); R. C. Larock and D. E. Stinn, Tetrahedron Lett., 30, 2767 (1989);
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    • J. Iqbal, B. Bhatia, and N. K. Nayyar, Chem. Rev., 94, 519 (1994); Palladium-catalyzed cyclization: R. C. Larock and D. E. Stinn, Tetrahedron Lett., 29, 4687 (1988); R. C. Larock and S. Babu, Tetrahedron Lett., 28, 5291 (1987); R. C. Larock and D. E. Stinn, Tetrahedron Lett., 30, 2767 (1989);
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    • Larock, R.C.1    Stinn, D.E.2
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    • note
    • 2O provided 2-deuteriophenyl prenyl ether in 93% yield (> 98%d).
  • 44
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    • note
    • 3MnLi, formation of anionic species might compete with formation of a radical which is generated by single electron transfer form manganate(II) to halo ether.
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    • note
    • 3MnLi.
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    • Decomposition of the dialkylmanganese species has been reported. M. Tamura and J. Kochi, J. Organomet. Chem., 29, 111 (1971).
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    • Tamura, M.1    Kochi, J.2
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    • note
    • An alternative mechanism, an iodine-manganese exchange followed by anionic carbomanganation giving 8, could not be negated. A more detailed study is obviously necessary to conclude the mechanism.
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    • Examples of sequences: (1) radical cyclization, (2) reduction to an organometallic, and (3) electrophilic trapping: a) W. A. Nugent and T. V. RajanBabu, J. Am. Chem. Soc., 110, 8561 (1988); b) K. Takai, K. Nitta, O. Fujimura, and K. Utimoto, J. Org. Chem., 54, 4732 (1989);
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    • Nugent, W.A.1    Rajanbabu, T.V.2
  • 50
    • 33845183971 scopus 로고
    • Examples of sequences: (1) radical cyclization, (2) reduction to an organometallic, and (3) electrophilic trapping: a) W. A. Nugent and T. V. RajanBabu, J. Am. Chem. Soc., 110, 8561 (1988); b) K. Takai, K. Nitta, O. Fujimura, and K. Utimoto, J. Org. Chem., 54, 4732 (1989);
    • (1989) J. Org. Chem. , vol.54 , pp. 4732
    • Takai, K.1    Nitta, K.2    Fujimura, O.3    Utimoto, K.4
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    • See Ref. 7
    • c) See Ref. 7.
  • 52
    • 85033146790 scopus 로고    scopus 로고
    • note
    • 2 afforded only the reduced product, phenyl prenyl ether, or N,N-diprenylaniline in 20 or 30% yield along with the recovered starting materials.
  • 53
    • 85033141775 scopus 로고    scopus 로고
    • note
    • 2) by oxygen to complete a catalytic cycle.
  • 59
    • 85033127509 scopus 로고    scopus 로고
    • note
    • 3B afforded 12g in 99% yield (E/Z = 44/56) (Chart 1). Chemical equations presented
  • 61
    • 0027986915 scopus 로고    scopus 로고
    • Recently nickel or cobalt-catalyzed radical cyclization reaction has been reported. A. Vaupel and P. Knochel, Tetrahedron Lett., 35, 8349 (1994); T. Bamhaoud and J. Prandi, J. Chem. Soc., Chem. Commun., 1996, 1229.
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    • Vaupel, A.1    Knochel, P.2
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    • Recently nickel or cobalt-catalyzed radical cyclization reaction has been reported. A. Vaupel and P. Knochel, Tetrahedron Lett., 35, 8349 (1994); T. Bamhaoud and J. Prandi, J. Chem. Soc., Chem. Commun., 1996, 1229.
    • J. Chem. Soc., Chem. Commun. , vol.1996 , pp. 1229
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  • 65
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    • note
    • In contrast to the catalytic reaction of 1a, in which the presence of oxygen was essential, the catalytic reaction of 11 was complete in 3 h at 0 °C under argon atmosphere in a sealed system. Thus, single electron transfer from zero-valent manganese to 2-iodoethanal acetal would provide alkyl radical and manganese(I) species as shown below (Chart 2). Chemical equations presented


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