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Volumn 129, Issue 21, 2007, Pages 6722-6723

Stable tetravalent phosphonium enolate zwitterions

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOLYTE; PHOSPHONIUM DERIVATIVE;

EID: 34249804781     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071990s     Document Type: Article
Times cited : (144)

References (34)
  • 1
    • 0037366617 scopus 로고    scopus 로고
    • For reviews on the Morita-Baylis-Hillman reaction, see: a
    • For reviews on the Morita-Baylis-Hillman reaction, see: (a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
    • (2003) Chem. Rev , vol.103 , pp. 811
    • Basavaiah, D.1    Rao, A.J.2    Satyanarayana, T.3
  • 4
    • 29244447356 scopus 로고
    • For reviews on phosphine-catalyzed reactions of activated allenes, see: a
    • For reviews on phosphine-catalyzed reactions of activated allenes, see: (a) Lu, X.; Du, Y.; Lu, C. Pure Appl. Chem. 2005, 77, 1985.
    • (1985) Pure Appl. Chem , vol.2005 , pp. 77
    • Lu, X.1    Du, Y.2    Lu, C.3
  • 13
    • 34249810704 scopus 로고    scopus 로고
    • Attempts to isolate or observe the 1:1 dipolar adducts of various trialkylphosphines and allenoates led only to oligomerization of the allenoates and recovery of the phosphines
    • Attempts to isolate or observe the 1:1 dipolar adducts of various trialkylphosphines and allenoates led only to oligomerization of the allenoates and recovery of the phosphines.
  • 14
    • 0011906533 scopus 로고    scopus 로고
    • 5, see: (a) Wittig, G.; Rieber, M. Naturwissenschaften 1948, 35, 345.
    • 5, see: (a) Wittig, G.; Rieber, M. Naturwissenschaften 1948, 35, 345.
  • 24
    • 0039087511 scopus 로고    scopus 로고
    • One exception is noted from Ramirez's studies, in which the 1:1 adduct formed between a trialkylphosphine and 3-benzylidene-2,4-pentanedione was reported to be a dipolar ion: (a) Ramirez, F.; Pilot, J. F.; Smith, C. P. Tetrahedron 1968, 24, 3735.
    • One exception is noted from Ramirez's studies, in which the 1:1 adduct formed between a trialkylphosphine and 3-benzylidene-2,4-pentanedione was reported to be a dipolar ion: (a) Ramirez, F.; Pilot, J. F.; Smith, C. P. Tetrahedron 1968, 24, 3735.
  • 27
    • 34249783977 scopus 로고    scopus 로고
    • To the best of our knowledge, this phosphonium enolate zwitterion is the first to have been characterized using X-ray crystallography
    • To the best of our knowledge, this phosphonium enolate zwitterion is the first to have been characterized using X-ray crystallography.
  • 28
    • 11344284526 scopus 로고    scopus 로고
    • The average trigonal bipyramidal phosphorane P-O distances measured from 20 crystalline organic compounds are 1.689 ± 0.024 Å (axial) and 1.619 ± 0.024 Å (equatorial); see: Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc, Perkin Trans. 2 1987, S1.
    • The average trigonal bipyramidal phosphorane P-O distances measured from 20 crystalline organic compounds are 1.689 ± 0.024 Å (axial) and 1.619 ± 0.024 Å (equatorial); see: Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc, Perkin Trans. 2 1987, S1.
  • 31
    • 0000144501 scopus 로고    scopus 로고
    • This situation is reminiscent of the stabilization of betaine intermediates in Wittig reactions employing PMe3 rather than PPh 3; see: Wittig, G, Rieber, M. Liebigs Ann. Chem. 1949, 562, 177
    • 3; see: Wittig, G.; Rieber, M. Liebigs Ann. Chem. 1949, 562, 177.
  • 34
    • 34249799960 scopus 로고    scopus 로고
    • Trace amounts (0.5-7%) of a product containing two units from 4-pyridinecarboxaldehyde and one from methyl propiolate were isolated from several of the reactions. The formation of this product can be rationalized from consideration of our proposed mechanism; see the Supporting Information for details.
    • Trace amounts (0.5-7%) of a product containing two units from 4-pyridinecarboxaldehyde and one from methyl propiolate were isolated from several of the reactions. The formation of this product can be rationalized from consideration of our proposed mechanism; see the Supporting Information for details.


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