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2
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85153185546
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Academic Press, New York, 139ff, 329ff
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a) P. W. Jolly, G. Wilke, The Organic Chemistry of Nickel, Academic Press, New York, 1974, vol. 1. pp. 110ff., 139ff., 329ff.;
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(1974)
The Organic Chemistry of Nickel
, vol.1
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Jolly, P.W.1
Wilke, G.2
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3
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34347267538
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Academic Press, New York
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b) P. W. Jolly, G. Wilke, The Organic Chemistry of Nickel, Academic Press, New York, 1975, vol. 2, p. 400.
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(1975)
The Organic Chemistry of Nickel
, vol.2
, pp. 400
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Jolly, P.W.1
Wilke, G.2
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5
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85153313533
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J. J. Eisch, L. E. Hallenbeck, K. I. Han, J. Am. Chem. Soc. 1986, 108, 7163-7761.
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(1986)
J. Am. Chem. Soc
, vol.108
, pp. 7163-7761
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Eisch, J.J.1
Hallenbeck, L.E.2
Han, K.I.3
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8
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0030593219
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J. J. Eisch, Y. Qian, M. Singh, J. Organomet. Chem. 1996, 512, 207-217.
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(1996)
J. Organomet. Chem
, vol.512
, pp. 207-217
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Eisch, J.J.1
Qian, Y.2
Singh, M.3
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9
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85153323478
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13C NMR evidence justifying the ylide resonance structure 22c as the paramount contributor to the π-electron distribution of this molecule:
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13C NMR evidence justifying the ylide resonance structure 22c as the paramount contributor to the π-electron distribution of this molecule:
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12
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85153255187
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the preparative procedure for 21 has been developed in this laboratory and is published here for the first time.
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b) the preparative procedure for 21 has been developed in this laboratory and is published here for the first time.
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14
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0001078954
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a) H. L. Ammon, G. L. Wheeler, P. H. Waats Jr, J. Am. Chem. Soc. 1973, 95, 6158-6163;
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(1973)
J. Am. Chem. Soc
, vol.95
, pp. 6158-6163
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Ammon, H.L.1
Wheeler, G.L.2
Waats Jr, P.H.3
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15
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85153203663
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[11a], such percentages for 24 ranged from 20% to 80%, depending upon the method of calculation.
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[11a], such percentages for 24 ranged from 20% to 80%, depending upon the method of calculation.
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16
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85153319580
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S. Neander, F. E. Tio, R. Buschman, U. Behrens, F. Olbrich, J. Organomet. Chem. 1999, 582, 58-65. For the potassium (18-crown-6) salt the C-C bonds range from 1.371-1.411 Å.
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S. Neander, F. E. Tio, R. Buschman, U. Behrens, F. Olbrich, J. Organomet. Chem. 1999, 582, 58-65. For the potassium (18-crown-6) salt the C-C bonds range from 1.371-1.411 Å.
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17
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34347211676
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a) L. M. Engelhardt, R. I. Papasergio, C. L. Raston, G. Salem, C. R. Whitaker, J. Chem. Soc. Dalton Trans. 1987, 1647-1653;
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(1987)
J. Chem. Soc. Dalton Trans
, pp. 1647-1653
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Engelhardt, L.M.1
Papasergio, R.I.2
Raston, C.L.3
Salem, G.4
Whitaker, C.R.5
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18
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85153255362
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13C NMR signals) of the aromatic carbon atom directly attached to the substituent have been correlated with substituent electronegativity after correcting for magnetic anisotropy effects. On the Allred-Rochow scale phosphorus at 2.06 is electron-releasing relative to carbon at 2.50 and thus magnetically shielding towards carbon.
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13C NMR signals) of the aromatic carbon atom directly attached to the substituent have been correlated with substituent electronegativity after correcting for magnetic anisotropy effects". On the Allred-Rochow scale phosphorus at 2.06 is electron-releasing relative to carbon at 2.50 and thus magnetically shielding towards carbon.
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19
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85153173590
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A referee has been helpful in suggesting the possibility of path b as an alternative possibility for producing 22c from 19 and 20 without the intermediacy of a nickel(II)-carbene. In addition, the same referee suggested the key experiment for deciding on the viability of path b as a competing mechanism, namely whether or not 19 and 20a would react with each other at 25°C
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A referee has been helpful in suggesting the possibility of path b as an alternative possibility for producing 22c from 19 and 20 without the intermediacy of a nickel(II)-carbene. In addition, the same referee suggested the key experiment for deciding on the viability of path b as a competing mechanism, namely whether or not 19 and 20a would react with each other at 25°C.
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21
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85153240537
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Although this report appeared 50 years ago, it has not been repudiated since and in fact is treated as reliable in a classic monograph on organophosphorus reactions: R. F. Hudson, Structure and Mechanism in Organo-Phosphorus Chemistry, Academic Press, New York, 1965, pp. 297-299
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b) Although this report appeared 50 years ago, it has not been repudiated since and in fact is treated as reliable in a classic monograph on organophosphorus reactions: R. F. Hudson, Structure and Mechanism in Organo-Phosphorus Chemistry, Academic Press, New York, 1965, pp. 297-299.
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22
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85153235442
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When the THF solution of the final reaction mixture was concentrated to half its and then cooled to 0°C, dark red crystals of bis(triethylphosphane)nickel(II) chloride were deposited, mp. 113-115°C 68, D. T. Doughty, G. Gordon, R. P. Stewart Jr, J. Am. Chem. Soc. 1979, 101, 2645-2648
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When the THF solution of the final reaction mixture was concentrated to half its volume and then cooled to 0°C, dark red crystals of bis(triethylphosphane)nickel(II) chloride were deposited, mp. 113-115°C (68%); D. T. Doughty, G. Gordon, R. P. Stewart Jr, J. Am. Chem. Soc. 1979, 101, 2645-2648.
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23
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85153308272
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A referee has proposed that in such coupling reactions of geminal dihalides with (Et3P)4Ni (20) perhaps metal carbenes are not involved at all, that maybe they are just phosphonium ylide adducts, R3P+-CR2--NiCl2 and, as Milstein and co-workers have shown, that ylides could be converted to metal-carbenes by late transition metal compounds (M. Gandelman, K. M. Naing, B. Rybtchinski, E. Poverenov, Y. Ben-David, N. Ashkenazi, R. M. Gauvin, D. Milstein, J. Am. Chem. Soc. 2005, 127, 15265-15272, Admittedly, our work has shown that phosphonium ylide 22c is readily formed from dibromo compound 19 and (Et3P)4Ni (20) and that 30 and 20 produce Wittig reagent 37 in solution, which is capable of being captured in a Wittig reaction with benzophenone. Despite the presence of 37 in such reactions, such phosphonium ylides or th
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3P): (Chemical Equation Presented)
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24
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85153179682
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4-tetraphenylcyclobutadiene-nickel(II) bromide where the two units of the monomer are held together by two Ni⋯Br⋯Ni bridges.
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4-tetraphenylcyclobutadiene-nickel(II) bromide where the two units of the monomer are held together by two Ni⋯Br⋯Ni bridges.
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25
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85153187145
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The failure to detect triphenylethylene in this trapping experiment with benzaldehyde can stem from either of two causes: (1) the supposed ylide, Ph 2C=PEt2, is too slow to react with PhCHO, before it reacts thus: Ph2C=PEt3, Ph2C(Cl)NiCl → Ph 2C=CPh2, Et3P)2NiCl2; or (2) in analogy with Scheme 7, Et3P is unable, for steric reasons, to react with Ph2C-NiCl2 (36) before coupling occurs via 38
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2 (36) before coupling occurs via 38.
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26
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85153220104
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3) and the mass spectrum of the mixture: MS (70eV): m/z = 270 [M], 179, 178, 152, 89, 77, Masters Thesis, SUNY-Binghamton
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3) and the mass spectrum of the mixture: MS (70eV): m/z = 270 [M], 179, 178, 152, 89, 77 (Y. Qian, Masters Thesis, SUNY-Binghamton, 1992, p. 57;
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(1992)
, pp. 57
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Qian, Y.1
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85153285280
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Y. Qian, Research Notebook No. 1, May 22, 1991, p. 36.
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Y. Qian, Research Notebook No. 1, May 22, 1991, p. 36).
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85153245167
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[7]; Y. Qian, Doctoral Dissertation, SUNY-Binghamton, 1996, pp. 117-118;
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[7]; Y. Qian, Doctoral Dissertation, SUNY-Binghamton, 1996, pp. 117-118;
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85153229636
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Y. Qian, Research Notebook No. 1, October 19, 1991, p. 66. The detailed mechanisms of these carbenoid oligomerizations are under further investigation.
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Y. Qian, Research Notebook No. 1, October 19, 1991, p. 66). The detailed mechanisms of these carbenoid oligomerizations are under further investigation.
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30
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0012006921
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Academic Press, New York
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J. J. Eisch, Organometallic Syntheses, Academic Press, New York, 1981, vol. 2, pp. 1-84.
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(1981)
Organometallic Syntheses
, vol.2
, pp. 1-84
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Eisch, J.J.1
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34
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0000840353
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E. Dinjus, I. Gorski, E. Uhlig, H. Walther, Z. Anorg. Allg. Chem. 1976, 75, 422-428.
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(1976)
Z. Anorg. Allg. Chem
, vol.75
, pp. 422-428
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Dinjus, E.1
Gorski, I.2
Uhlig, E.3
Walther, H.4
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35
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0001573415
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T. Yamamoto, T. Kohara, K. Osakada, A. Yamamota, Bull. Chem. Soc. Jpn. 1983, 56, 2147-2153.
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(1983)
Bull. Chem. Soc. Jpn
, vol.56
, pp. 2147-2153
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Yamamoto, T.1
Kohara, T.2
Osakada, K.3
Yamamota, A.4
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