Mechanism of the reaction of vinyl chloride with (α-diimine)PdMe + species

Organometallics

Volumn 29, Issue 7, 2010, Pages 1750-1760

  Kilyanek, Stefan M ^a   Stoebenau, Edward J ^a   Vinayavekhin, Nawaporn ^a   Jordan, Richard F ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL RESULTS; DFT COMPUTATIONS; DIIMINES; ISOTOPE LABELING; OXIDATIVE ADDITIONS; VINYL CHLORIDES;

CHLORINE COMPOUNDS; DEUTERIUM; ISOMERS; LABELING; PALLADIUM; PROPYLENE;

REACTION KINETICS;

EID: 77950841805     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1000925     Document Type: Article

References (126)

1. Odian, G. Principles of Polymerization; Wiley & Sons: New York, 1991; pp 308-310 and 712?713.
2. Vinyl Chloride and Poly(Vinyl Chloride). Kirk-Othmer Encyclopedia of Chemical Technology, 3 rd ed.; Wiley & Sons: New York, 1983; Vol. 23, pp 865-936.
3. Alger, M. Polymer Science Dictionary, 2 nd ed.; Chapman & Hall: New York, 1997; pp 462-463.
4. Doak, K. W. In Encyclopedia of Polymer Science and Engineering, 2 nd ed.
5. Klingsberg, A. and Muldoon, A., Eds.; Wiley: New York, 1986; Vol. 6, p 383.
6. Sianesi, D.; Caporiccio, G. J. Polym. Sci., Part A 1968, 6, 335
7. Burkhart, R. D.; Zutty, N. L. J. Polym. Sci., Part A 1963, 1, 1137
8. Donskoi, A. A.; Shashkina, M. A.; Zaikov, G. E. New Concenpts in Polymer Science: Fire Resistant and Thermally Stable Materials Derived from Chlorinated Polyethylene; VSP BV: The Netherlands, 2003; pp 42-48.
9. Chang, B. H.; Zeigler, R.; Hiltner, A. Polym. Eng. Sci. 1988, 28, 1167
10. Zhao, J.; Li, J.; Feng, Y.; Yin, J. Polym. Adv. Technol. 2007, 18, 822
11. Boz, E.; Nemeth, A. J.; Ghiviriga, I.; Jeon, K.; Alamo, R. G.; Wagener, K. B. Macromolecules 2007, 40, 6545
12. Boz, E.; Nemeth, A. J.; Alamo, R. G.; Wagener, K. B. Adv. Synth. Catal. 2007, 349, 137
13. Boz, E.; Wagener, K. B.; Ghosal, A.; Fu, R.; Alamo, R. G. Macromolecules 2006, 39, 4437
14. Hillmeyer, M. A.; Laredo, W. R.; Grubbs, R. H. Macromolecules 1995, 28, 6311
15. Yang, H.; Islam, M.; Budde, C.; Rowan, S. J. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 2107
16. Schilling, F. C.; Tonelli, A. E.; Valenciano, M. Macromolecules 1985, 18, 356
17. Stockland, R. A., Jr.; Foley, S. R.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 796
18. Stockland, R. A., Jr.; Jordan, R. F. J. Am. Chem. Soc. 2000, 122, 6315
19. Gaynor, S. G. Macromolecules 2003, 36, 4692
20. Foley, S. R.; Stockland, R. A., Jr.; Shen, H.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 4350
21. Kang, M.; Sen, A.; Zakharov, L.; Rheingold, A. L. J. Am. Chem. Soc. 2002, 124, 12080
22. Weng, W.; Shen., Z.; Jordan, R. F. J. Am. Chem. Soc. 2007, 129, 15450
23. Watson, L. A.; Yandulov, D. V.; Caulton, K. G. J. Am. Chem. Soc. 2001, 123, 603
24. Strazisar, S. A.; Wolczanski, P. T. J. Am. Chem. Soc. 2001, 123, 4728
25. Wu, F.; Dash, A. K.; Jordan, R. F. J. Am. Chem. Soc. 2004, 126, 15360
26. For other studies of β-X elimination see: Eisenstein, O.; Crabtree, R. H. New J. Chem. 2001, 25, 665
27. Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156
28. Clot, E.; Megret, C.; Kraft, B. M.; Eisenstein, O.; Jones, W. D. J. Am. Chem. Soc. 2004, 126, 5647
29. Lei, A.; Lui, G.; Lu, X. J. Org. Chem. 2002, 67, 974
30. Zhang, Z.; Lu, X.; Xu, Z.; Zhang, Q.; Han, X. Organometallics 2001, 21, 3724
31. Liu, G.; Lu, X. Tetrahedron Lett. 2002, 6791
32. León, E. I.; Paz, N. R.; Riesco-Fagundo, C.; Suúrez, E. Tetrahedron 2008, 10706
33. Zhu, G.; Zhang, Z. J. Org. Chem. 2005, 70, 3339
34. Zhao, H.; Ariafard, A.; Liu, Z. Organometallics 2006, 26, 812
35. Cundari, T. R.; Taylor, C. D. Organometallics 2003, 23, 4047
36. Liu, G.; Lu, X. Tetrahedron Lett. 2003, 467
37. 2ScF and propylene via insertion and subsequent β-F elimination. Burger, B. Ph.D. Thesis, California Institute of Technology, 1987.
38. Halpern, J.; Jewsbury, R. A. J. Organomet. Chem. 1979, 181, 223
39. Fanizzi, F. P.; Maresca, L.; Pacifico, C.; Natile, G.; Lanfranchi, M.; Tiripicchio, A. Eur. J. Inorg. Chem. 1999, 38, 1351
40. Deeming, A. J.; Shaw, B. L. J. Chem. Soc. A 1971, 376
41. Mecking, S.; Johnson, L.; Wang, L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 888
42. Foley, S. R.; Shen, H.; Qadeer, U. A.; Jordan, R. F. Organometallics 2004, 23, 600
43. Axe, F. U.; Marynick, D. S. J. Am. Chem. Soc. 1988, 110, 3728
44. Cotton, J. D.; Markwell, R. D. J. Organomet. Chem. 1990, 388, 123
45. Cotton, J. D.; Crisp, G. T.; Daly, V. A. Inorg. Chim. Acta 1981, 47, 165
46. Cross, R. J.; Gemmill, J. J. Chem. Soc., Dalton Trans. 1981, 2317
47. Cawse, J. N.; Fiato, R. A.; Pruett, R. L. J. Organomet. Chem. 1979, 172, 405
48. Kuhlmann, E. J.; Alexander, J. J. Coord. Chem. Rev. 1980, 33, 195
49. Calderazzo, F.; Noack, K. Coord. Chem. Rev. 1966, 1, 118
50. Belderrain, T. R.; Grubbs, R. H. Organometallics 1997, 16, 4001
51. Wilhelm, T. E.; Belderrain, T. R.; Brown, S. N.; Grubbs, R. H. Organometallics 1997, 16, 3867
52. Olivan, M.; Caulton, K. G. Inorg. Chem. 1999, 38, 566
53. Feher, F. J.; Gergens, D. D.; Ziller, J. W. Organometallics 1993, 12, 2810
54. Goldman, A. S.; Tyler, D. R. Organometallics 1984, 3, 449
55. Heck, H. R. Acc. Chem. Res. 1979, 12, 146
56. Stille, J. K.; Lau, K. S. Y. Acc. Chem. Res. 1977, 10, 434
57. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1977, 99, 2501
58. Labinger, J. A.; Osborn, J. A.; Coville, N. J. Inorg. Chem. 1980, 19, 3236
59. Brown, J. M.; Cooley, N. A. J. Chem. Soc., Chem. Commun. 1988, 1345
60. Jutand, A.; Négri, S. Organometallics 2003, 22, 4229
61. Álvarez, R.; Faza, O. N.; López, C. S.; de Lera, A. R. Org. Lett. 2006, 8, 35
62. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644
63. Arnold, P. L.; Sanford, M. S.; Pearson, S. M. J. Am. Chem. Soc. 2009, 131, 13912
64. Welbes, L. L.; Lynos, T. W.; Cychosz, K. A.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 5836, and refrences therein.
65. Philipp, D. M.; Muller, R. P.; Goddard, W. A.; Storer, J.; McAdon, M.; Mullins, M. J. Am. Chem. Soc. 2002, 124, 10198
66. Szabo, M. J.; Jordan, R. F.; Michalak, A.; Piers, W. E.; Weiss, T.; Yang, S.; Ziegler, T. Organometallics 2004, 23, 5565
67. Mitoraj, M.; Michalak, A. J. Mol. Model. 2005, 11, 341
68. von Schenck, H.; Stromberg, S.; Zetterberg, K.; Ludwig, M.; Akermark, B.; Svensson, M. Organometallics 2001, 20, 2813
69. D values for β-H eliminations are in the range 2.0?5.6. Mak, K. W.; Chan, K. S. J. Am. Chem. Soc. 1998, 120, 9686
70. Burger, B. J.; Thompson, M. E.; Cotter, W. D.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 1566
71. Ikariya, T.; Yamamoto, A. J. Organomet. Chem. 1976, 120, 257
72. Evans, J.; Schwartz, J.; Urquhart, P. W. J. Organomet. Chem. 1974, 81, C37
73. + yields a ca. 2:1 mixture of trans- and cis -2-butene, along with 1-butene: Rix, F. C.; Brookhart, M.; White, P. S. J. Am. Chem. Soc. 1996, 118, 4746
74. 1 in the mass spectrum, this could not be determined.
75. No polyvinyl chloride is formed in these reactions, even when a large excess of vinyl chloride is used, which argues against mechanisms involving free radicals.
76. Frisch; et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004. See the Supporting Information for the complete citation.
77. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
78. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
79. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200
80. Rassolov, V. A.; Ratner, M. A.; Pople, J. A.; Redfern, P. C.; Curtiss, L. A. J. Comput. Chem. 2001, 22, 976
81. Rassolov, V. A.; Pople, J. A.; Ratner, M. A.; Windus, T. L. J. Chem. Phys. 1998, 109, 1223
82. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270
83. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284
84. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299
85. transfer? Cl (125°) angles are within the range observed for C?H--Cl?M hydrogen bonds. Aullon, G.; Bellamy, D.; Orpen, A. G.; Brammer, L.; Bruton, E. A. Chem. Commun. 1998, 653
86. Brammer, L.; Bruton, E. A.; Sherwood, P. Cryst. Growth Des. 2001, 1, 277
87. Nouri, D. H.; Tantillo, D. J. J. Org. Chem. 2006, 71, 3686
88. Domingo, L. R. J. Org. Chem. 2001, 66, 3211
89. Kalaiselvan, A.; Ammal, S. C.; Venuvanalingam, P.; Yamataka, H. J. Phys. Chem. A. 2005, 109, 4829
90. Ding, L.; Chen, X.; Fang, W. H. Org. Lett. 2009, 11, 1495
91. H-shift is similar to that of the trans-sec -butyl cation. Vrcek, V.; Kronja, O.; Saunders, M. J. Chem. Theory Comput. 2007, 3, 1223
92. Quintal, M. A.; Karton, A.; Iron, M. A.; Boese, A. D.; Martin, J. M. L. J. Phys. Chem. A 2006, 110, 709
93. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865 Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1997, 78, 1396
94. The barrier for 2,1-insertion calculated for the full system at the PBE0 level of theory is 13.4 kcal/mol.
95. Karton, A.; Tarnopolsky, A.; Lamère, J.; Schatz, G. C.; Martin, J. M. L. J. Phys. Chem. A 2008, 112, 12868
96. Korth, M.; Grimme, S. J. Chem. Theory Comput. 2009, 5, 993
97. An analogous mechanism involving 2,1-insertion into the Pd?H bond is also possible. However, this mechanism predicts dueterium enrichment in the propene methyl group, which could not be conclusively detected.
98. Francis, J. E.; Leitch, L. C. J. Can. Chem. 1957, 35, 500
99. Hart, D. W.; Blackburn, T. F.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 679
100. Schottek, J.; Röttger, D.; Erker, G.; Fröhlich, R. J. Am. Chem. Soc. 1998, 120, 5264
101. Erker, G.; Kropp, K.; Atwood, J. L.; Hunter, W. E. Organometallics 1983, 2, 1555
102. Buchwald, S. L.; LaMaire, S. J.; Nielson, R. B.; Watson, B. T.; King, S. M. Org. Synth. 1993, 71, 77
103. McCord, E. F.; McLain, S. J.; Nelson, L. T. J.; Arthur, S. D.; Coughlin, E. B.; Ittel, S. D.; Johnson, L. K.; Tempel, D.; Killian, C. M.; Brookhart, M. Macromolecules 2001, 34, 362
104. Johnson, L. K.; Kilian, C. M.; Arthur, S. D.; Feldman, J.; Mccord, E. F.; Mclain, S. J.; Kreutzer, K. A.; Bennett, M. A.; Coughlin, E. B. PCT Int. Appl. WO9623010, 1996.
105. Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414
106. Yanagisawa, M.; Shimamura, T.; Iida, D.; Matsua, J.; Mukaiyama, T. Chem. Pharm. Bull. 2000, 48, 1838
107. Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502
108. Bylaska, E. J.; et al. NWChem, A Computational Chemistry Package for Parallel Computers, Version 5.1.1; Pacific Northwest National Laboratory: Richland, WA, 2009. A modified version. See the Supporting Information for the complete citation.
109. Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49
110. Peng, C.; Schlegel, H. B. Isr. J. Chem. 1993, 33, 449
111. For the 6-311++G* basis set see: Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
112. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W; Schleyer, P. V. R. J. Comput. Chem. 1983, 4, 294
113. For the cc-pVTZ and cc-pVTZ-PP basis sets see: Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007
114. Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1994, 100, 2975
115. Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 1358
116. Wilson, A. K.; Woon, D. E.; Peterson, K. A.; Dunning, T. H., Jr. J. Chem. Phys. 1999, 110, 7667
117. de Jong, W. A.; Harrison, R. J.; Dixon, D. A. J. Chem. Phys. 2001, 114, 48
118. Balabanov, N. B.; Peterson, K. A. J. Chem. Phys. 2005, 123, 064107
119. Peterson, K. A.; Figgen, D.; Dolg, M.; Stoll, H. J. Chem. Phys. 2007, 126, 124101
120. For the SDD basis set see: Bergner, A.; Dolg, M.; Kuechle, W.; Stoll, H.; Preuss, H. Mol. Phys. 1993, 80, 1431
121. Kaupp, M.; Schleyer, P. v. R.; Stoll, H.; Preuss, H. J. Chem. Phys. 1991, 94, 1360
122. Dolg, M.; Stoll, H.; Preuss, H.; Pitzer, R. M. J. Phys. Chem. 1993, 97, 5852
123. For a description of added [2f1g] valence functions see: Martin, J. M. L.; Sundermann, A. J. Chem. Phys. 2001, 114, 3408
124. For a description of the additional diffuse functions see the description of the AVTZ basis set in ref 36.
125. Flükiger, P.; Lüthi, H. P.; Portmann, S.;; Weber, J. MOLEKEL 4.3; Swiss Center for Scientific Computing: Manno, Switzerland, 2000?2002.
126. Portmann, S.; Lüthi, H. P. MOLEKEL: An Interactive Molecular Graphics Tool. CHIMIA 2000, 54, 766. (Pubitemid 33204261)