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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
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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.
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14
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5, see: (a) Wittig, G.; Rieber, M. Naturwissenschaften 1948, 35, 345.
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5, see: (a) Wittig, G.; Rieber, M. Naturwissenschaften 1948, 35, 345.
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(a) Ramirez, F.; Madan, O. P.; Heller, S. R. J. Am. Chem. Soc. 1965, 87, 731.
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0039087511
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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.
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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.
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25
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(b) Ramirez, F.; Pilot, J. F.; Madan, O. P.; Smith, C. P. J. Am. Chem. Soc. 1968, 90, 1275.
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85052463354
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31P NMR Data of Four Coordinate Phosphonium Salts and Betaines
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Tebby, J. C, Ed, CRC Press: Boca Raton, FL
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31P NMR Data of Four Coordinate Phosphonium Salts and Betaines. In Handbook of Phosphorus-31 Nuclear Magnetic Resonance Data; Tebby, J. C., Ed.; CRC Press: Boca Raton, FL, 1991; pp 181-226.
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Hudson, H.R.1
Dillon, K.B.2
Walker, B.J.3
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27
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34249783977
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To the best of our knowledge, this phosphonium enolate zwitterion is the first to have been characterized using X-ray crystallography
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To the best of our knowledge, this phosphonium enolate zwitterion is the first to have been characterized using X-ray crystallography.
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11344284526
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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.
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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.
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(a) Vedejs, E.; Steck, P. L. Angew. Chem., Int. Ed. 1999, 38, 2788
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0000144501
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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
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3; see: Wittig, G.; Rieber, M. Liebigs Ann. Chem. 1949, 562, 177.
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(a) Nozaki, K.; Sato, N.; Ikeda, K.; Takaya, H. J. Org. Chem. 1996, 61, 4516.
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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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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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