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Volumn 23, Issue 8, 2004, Pages 1932-1946

Cleavage of Conjugated Alkenes by Cationic Osmium Nitrides: Scope of the Reaction and Dynamics of the Azaallenium Products

Author keywords

[No Author keywords available]

Indexed keywords

BACK-BONDING; CONJUGATED ALKENES; DOUBLE BONDS; STEREOISOMERIZATIONS;

EID: 2342428170     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om034404m     Document Type: Article
Times cited : (22)

References (49)
  • 20
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    • (1982) The Chemistry of the Allenes , vol.3 , pp. 775-884
    • Runge, W.1
  • 21
    • 0001724751 scopus 로고
    • 15d (a) Gasteiger, J.; Dammer, O. Tetrahedron 1978, 34, 2939-2945. (b) Angus, R. O., Jr.; Schmidt, M. W.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 532-537. (c) Bettinger, H. F.; Schleyer, P. v. R.; Schreiner, P. R.; Schaefer, H. F., III. J. Org. Chem. 1997, 62, 9267-9275. (d) Roth, W. R.; Adamczak, O.; Breuckmann, R.; Lennartz, H. W.; Boese, R. Chem. Ber. 1991, 124, 2499-2521.
    • (1978) Tetrahedron , vol.34 , pp. 2939-2945
    • Gasteiger, J.1    Dammer, O.2
  • 22
    • 0001529056 scopus 로고
    • 15d (a) Gasteiger, J.; Dammer, O. Tetrahedron 1978, 34, 2939-2945. (b) Angus, R. O., Jr.; Schmidt, M. W.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 532-537. (c) Bettinger, H. F.; Schleyer, P. v. R.; Schreiner, P. R.; Schaefer, H. F., III. J. Org. Chem. 1997, 62, 9267-9275. (d) Roth, W. R.; Adamczak, O.; Breuckmann, R.; Lennartz, H. W.; Boese, R. Chem. Ber. 1991, 124, 2499-2521.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 532-537
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  • 23
    • 0000958003 scopus 로고    scopus 로고
    • 15d (a) Gasteiger, J.; Dammer, O. Tetrahedron 1978, 34, 2939-2945. (b) Angus, R. O., Jr.; Schmidt, M. W.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 532-537. (c) Bettinger, H. F.; Schleyer, P. v. R.; Schreiner, P. R.; Schaefer, H. F., III. J. Org. Chem. 1997, 62, 9267-9275. (d) Roth, W. R.; Adamczak, O.; Breuckmann, R.; Lennartz, H. W.; Boese, R. Chem. Ber. 1991, 124, 2499-2521.
    • (1997) J. Org. Chem. , vol.62 , pp. 9267-9275
    • Bettinger, H.F.1    Schleyer, P.V.R.2    Schreiner, P.R.3    Schaefer III, H.F.4
  • 24
    • 0000617085 scopus 로고
    • 15d (a) Gasteiger, J.; Dammer, O. Tetrahedron 1978, 34, 2939-2945. (b) Angus, R. O., Jr.; Schmidt, M. W.; Johnson, R. P. J. Am. Chem. Soc. 1985, 107, 532-537. (c) Bettinger, H. F.; Schleyer, P. v. R.; Schreiner, P. R.; Schaefer, H. F., III. J. Org. Chem. 1997, 62, 9267-9275. (d) Roth, W. R.; Adamczak, O.; Breuckmann, R.; Lennartz, H. W.; Boese, R. Chem. Ber. 1991, 124, 2499-2521.
    • (1991) Chem. Ber. , vol.124 , pp. 2499-2521
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  • 27
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    • Taylor, S. D.; Brown, S. N. Unpublished results
    • Taylor, S. D.; Brown, S. N. Unpublished results.
  • 31
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    • Maestri, A. G.; Braunecker, W. A.; Brown, S. N. Manuscript in preparation
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  • 34
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    • Calculated using substituent constants in ref 21 and equilibrium data from: Toullec, J.; Bennour, S. J. Org. Chem. 1994, 59, 2831-2839.
    • (1994) J. Org. Chem. , vol.59 , pp. 2831-2839
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  • 45
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    • 1,4-Dimethyl-1,3-cyclohexadiene was used as a 2:1 mixture with 1,4-dimethyl-1,4-cyclohexadiene; control experiments show that the unconjugated diene is unreactive with 1 at room temperature. Preparation of the mixture of dienes: Brady, W. T.; Norton, S. J.; Ko, J. Synthesis 1985, 704-705.
    • (1985) Synthesis , pp. 704-705
    • Brady, W.T.1    Norton, S.J.2    Ko, J.3
  • 49
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    • Kluwer Academic Publishers: Dordrecht, The Netherlands
    • International Tables of Crystallography; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992; Vol. C.
    • (1992) International Tables of Crystallography , vol.100


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