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Volumn 63, Issue 14, 1998, Pages 4711-4716

Radical Cyclizations of Acylgermane Oxime Ethers and Hydrazones: Direct Routes to Cyclic Hydrazones and Oximes

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EID: 0000497268     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980369v     Document Type: Article
Times cited : (56)

References (48)
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    • Ph.D. Thesis, University of Pittsburgh
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    • (1996)
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    • Reference 11d
    • (b) Reference 11d.
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    • 3GeBr. See: Harris, D. M.; Nebergall, W. H.; Johnson, O. H. Inorg. Synth. 1957, 5, 70-72 and 76-78. We used a modification of this procedure as described in the Supporting Information.
    • (1957) Inorg. Synth. , vol.5 , pp. 70-72
    • Harris, D.M.1    Nebergall, W.H.2    Johnson, O.H.3
  • 29
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    • Acylsilicon, -germanium or boron functions
    • Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Elsevier Science, Inc.: New York, Chapter 5.09
    • Qi, H.; Curran, D. P. Acylsilicon, -germanium or boron functions. In Compr. Org. Funct. Group Transf., 1st ed.; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Elsevier Science, Inc.: New York, 1995; Vol. 4, Chapter 5.09, pp 409-433.
    • (1995) Compr. Org. Funct. Group Transf., 1st Ed. , vol.4 , pp. 409-433
    • Qi, H.1    Curran, D.P.2
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    • note
    • A catalytic amount of acid is not required, but it was essential to liberate the O-benzylhydroxylamine from the commercially available hydrochloride salt.
  • 33
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    • Similar reactivities have been observed with suitably substituted acylgermanes; see ref 6a and: Tsai, Y. M.; Niel, H. C.; Cherng, C. D. J. Org. Chem. 1992, 57, 7010-14.
    • (1992) J. Org. Chem. , vol.57 , pp. 7010-7014
    • Tsai, Y.M.1    Niel, H.C.2    Cherng, C.D.3
  • 36
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    • Stereoselective Synthesis
    • Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: New York
    • Configurational assignment of hydrazone/oxime double bond isomers: (a) Duddeck, H. Stereoselective Synthesis. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: New York, 1995; Vol. E21a, pp 324-327. (b) Bunnell, C. A.; Fuchs, P. L. J. Org. Chem. 1977, 42, 2614-2617.
    • (1995) Methods of Organic Chemistry (Houben-Weyl) , vol.E21A , pp. 324-327
    • Duddeck, H.1
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    • Configurational assignment of hydrazone/oxime double bond isomers: (a) Duddeck, H. Stereoselective Synthesis. Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: New York, 1995; Vol. E21a, pp 324-327. (b) Bunnell, C. A.; Fuchs, P. L. J. Org. Chem. 1977, 42, 2614-2617.
    • (1977) J. Org. Chem. , vol.42 , pp. 2614-2617
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    • 3GeH presumably also occurred in previously reported kinetic experiments (see ref 1)
    • 3GeH presumably also occurred in previously reported kinetic experiments (see ref 1).
  • 44
    • 85034463775 scopus 로고    scopus 로고
    • note
    • (b) Reaction of triphenylgermanium bromide and AIBN with triphenyltin hydride provides triphenylgermanium hydride and triphenyltin bromide.
  • 45
    • 85034478940 scopus 로고    scopus 로고
    • note
    • 2=NOBn (HOMO -9.6920 eV, LUMO 0.2470 eV).
  • 46
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    • -1 at 80 °C. (a) Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739. (b) Walling, C.; Cioffari, A. J. Am. Chem. Soc. 1972, 94, 6059-64. (c) Carlsson, D. J.; Ingold, K. U. J. Am. Chem. Soc. 1968, 90, 7047-55.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 7739
    • Chatgilialoglu, C.1    Ingold, K.U.2    Scaiano, J.C.3
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    • -1 at 80 °C. (a) Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739. (b) Walling, C.; Cioffari, A. J. Am. Chem. Soc. 1972, 94, 6059-64. (c) Carlsson, D. J.; Ingold, K. U. J. Am. Chem. Soc. 1968, 90, 7047-55.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 6059-6064
    • Walling, C.1    Cioffari, A.2
  • 48
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    • -1 at 80 °C. (a) Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739. (b) Walling, C.; Cioffari, A. J. Am. Chem. Soc. 1972, 94, 6059-64. (c) Carlsson, D. J.; Ingold, K. U. J. Am. Chem. Soc. 1968, 90, 7047-55.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 7047-7055
    • Carlsson, D.J.1    Ingold, K.U.2


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