Energetics of metal-ligand multiple bonds. A combined solution thermochemical and ab initio quantum chemical study of M=O bonding in group 6 metallocene oxo complexes

Journal of the American Chemical Society

Volumn 120, Issue 13, 1998, Pages 3111-3122

  Luo, Lubin ^a   Lanza, Giuseppe ^b   Fragalà, Ignazio L ^c   Stern, Charlotte L ^a   Marks, Tobin J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b UNIVERSITY OF BASILICATA   (Italy)

^c UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX; METAL OXIDE; METALLOCENE OXO COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENERGY TRANSFER; LIGAND BINDING; METAL BINDING; MOLECULAR INTERACTION; STOICHIOMETRY; SYNTHESIS; THERMODYNAMICS;

EID: 0032495767     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971010b     Document Type: Article

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22. Group 6: (a) Henary, M.; Kaska, W. C.; Zink, J. I. Inorg. Chem. 1991, 30, 1674-1676. (b) Pilato, R. S.; Housmekerides, C. E.; Jernakoff, P.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1990, 9, 2333-2341. (c) Pilato, R. S.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Inorg. Chem. 1990, 29, 1986-1990. (d) Parkin, G.; Bercaw, J. E. J. Am. Chem. Soc. 1989, 111, 391-393. (e) Parkin, G.; Bercaw, J. E. Polyhedron 1988, 1, 2053-2082. (f) Parkin, G.; Marsh, R. E.; Schaefer, W. P.; Bercaw, J. E. Inorg. Chem. 1988, 27, 3262-3264. (g) Silavwe, N. D.; Bruce, M. R. M.; Philbin, C. E.; Tyler, D. R. Inorg. Chem. 1988, 27, 4669-4676. (h) Silavwe, N. D.; Chiang, M. Y.; Tyler, D. R. Inorg. Chem. 1985, 24, 4219-4221. (i) Berry, M.; Davies, S. G.; Green, M. L. H. J. Chem. Soc., Chem. Commun. 1978, 99-100. (j) Green, M. L. H.; Lynch, A. H.; Swanwick, M. G. J. Chem. Soc., Dalton Trans. 1972, 1445-1447.
23. Group 6: (a) Henary, M.; Kaska, W. C.; Zink, J. I. Inorg. Chem. 1991, 30, 1674-1676. (b) Pilato, R. S.; Housmekerides, C. E.; Jernakoff, P.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1990, 9, 2333-2341. (c) Pilato, R. S.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Inorg. Chem. 1990, 29, 1986-1990. (d) Parkin, G.; Bercaw, J. E. J. Am. Chem. Soc. 1989, 111, 391-393. (e) Parkin, G.; Bercaw, J. E. Polyhedron 1988, 1, 2053-2082. (f) Parkin, G.; Marsh, R. E.; Schaefer, W. P.; Bercaw, J. E. Inorg. Chem. 1988, 27, 3262-3264. (g) Silavwe, N. D.; Bruce, M. R. M.; Philbin, C. E.; Tyler, D. R. Inorg. Chem. 1988, 27, 4669-4676. (h) Silavwe, N. D.; Chiang, M. Y.; Tyler, D. R. Inorg. Chem. 1985, 24, 4219-4221. (i) Berry, M.; Davies, S. G.; Green, M. L. H. J. Chem. Soc., Chem. Commun. 1978, 99-100. (j) Green, M. L. H.; Lynch, A. H.; Swanwick, M. G. J. Chem. Soc., Dalton Trans. 1972, 1445-1447.
24. Group 6: (a) Henary, M.; Kaska, W. C.; Zink, J. I. Inorg. Chem. 1991, 30, 1674-1676. (b) Pilato, R. S.; Housmekerides, C. E.; Jernakoff, P.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1990, 9, 2333-2341. (c) Pilato, R. S.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Inorg. Chem. 1990, 29, 1986-1990. (d) Parkin, G.; Bercaw, J. E. J. Am. Chem. Soc. 1989, 111, 391-393. (e) Parkin, G.; Bercaw, J. E. Polyhedron 1988, 1, 2053-2082. (f) Parkin, G.; Marsh, R. E.; Schaefer, W. P.; Bercaw, J. E. Inorg. Chem. 1988, 27, 3262-3264. (g) Silavwe, N. D.; Bruce, M. R. M.; Philbin, C. E.; Tyler, D. R. Inorg. Chem. 1988, 27, 4669-4676. (h) Silavwe, N. D.; Chiang, M. Y.; Tyler, D. R. Inorg. Chem. 1985, 24, 4219-4221. (i) Berry, M.; Davies, S. G.; Green, M. L. H. J. Chem. Soc., Chem. Commun. 1978, 99-100. (j) Green, M. L. H.; Lynch, A. H.; Swanwick, M. G. J. Chem. Soc., Dalton Trans. 1972, 1445-1447.
25. Group 6: (a) Henary, M.; Kaska, W. C.; Zink, J. I. Inorg. Chem. 1991, 30, 1674-1676. (b) Pilato, R. S.; Housmekerides, C. E.; Jernakoff, P.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1990, 9, 2333-2341. (c) Pilato, R. S.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Inorg. Chem. 1990, 29, 1986-1990. (d) Parkin, G.; Bercaw, J. E. J. Am. Chem. Soc. 1989, 111, 391-393. (e) Parkin, G.; Bercaw, J. E. Polyhedron 1988, 1, 2053-2082. (f) Parkin, G.; Marsh, R. E.; Schaefer, W. P.; Bercaw, J. E. Inorg. Chem. 1988, 27, 3262-3264. (g) Silavwe, N. D.; Bruce, M. R. M.; Philbin, C. E.; Tyler, D. R. Inorg. Chem. 1988, 27, 4669-4676. (h) Silavwe, N. D.; Chiang, M. Y.; Tyler, D. R. Inorg. Chem. 1985, 24, 4219-4221. (i) Berry, M.; Davies, S. G.; Green, M. L. H. J. Chem. Soc., Chem. Commun. 1978, 99-100. (j) Green, M. L. H.; Lynch, A. H.; Swanwick, M. G. J. Chem. Soc., Dalton Trans. 1972, 1445-1447.
26. Group 6: (a) Henary, M.; Kaska, W. C.; Zink, J. I. Inorg. Chem. 1991, 30, 1674-1676. (b) Pilato, R. S.; Housmekerides, C. E.; Jernakoff, P.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1990, 9, 2333-2341. (c) Pilato, R. S.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Inorg. Chem. 1990, 29, 1986-1990. (d) Parkin, G.; Bercaw, J. E. J. Am. Chem. Soc. 1989, 111, 391-393. (e) Parkin, G.; Bercaw, J. E. Polyhedron 1988, 1, 2053-2082. (f) Parkin, G.; Marsh, R. E.; Schaefer, W. P.; Bercaw, J. E. Inorg. Chem. 1988, 27, 3262-3264. (g) Silavwe, N. D.; Bruce, M. R. M.; Philbin, C. E.; Tyler, D. R. Inorg. Chem. 1988, 27, 4669-4676. (h) Silavwe, N. D.; Chiang, M. Y.; Tyler, D. R. Inorg. Chem. 1985, 24, 4219-4221. (i) Berry, M.; Davies, S. G.; Green, M. L. H. J. Chem. Soc., Chem. Commun. 1978, 99-100. (j) Green, M. L. H.; Lynch, A. H.; Swanwick, M. G. J. Chem. Soc., Dalton Trans. 1972, 1445-1447.
27. Group 6: (a) Henary, M.; Kaska, W. C.; Zink, J. I. Inorg. Chem. 1991, 30, 1674-1676. (b) Pilato, R. S.; Housmekerides, C. E.; Jernakoff, P.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1990, 9, 2333-2341. (c) Pilato, R. S.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Inorg. Chem. 1990, 29, 1986-1990. (d) Parkin, G.; Bercaw, J. E. J. Am. Chem. Soc. 1989, 111, 391-393. (e) Parkin, G.; Bercaw, J. E. Polyhedron 1988, 1, 2053-2082. (f) Parkin, G.; Marsh, R. E.; Schaefer, W. P.; Bercaw, J. E. Inorg. Chem. 1988, 27, 3262-3264. (g) Silavwe, N. D.; Bruce, M. R. M.; Philbin, C. E.; Tyler, D. R. Inorg. Chem. 1988, 27, 4669-4676. (h) Silavwe, N. D.; Chiang, M. Y.; Tyler, D. R. Inorg. Chem. 1985, 24, 4219-4221. (i) Berry, M.; Davies, S. G.; Green, M. L. H. J. Chem. Soc., Chem. Commun. 1978, 99-100. (j) Green, M. L. H.; Lynch, A. H.; Swanwick, M. G. J. Chem. Soc., Dalton Trans. 1972, 1445-1447.
28. Group 6: (a) Henary, M.; Kaska, W. C.; Zink, J. I. Inorg. Chem. 1991, 30, 1674-1676. (b) Pilato, R. S.; Housmekerides, C. E.; Jernakoff, P.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1990, 9, 2333-2341. (c) Pilato, R. S.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Inorg. Chem. 1990, 29, 1986-1990. (d) Parkin, G.; Bercaw, J. E. J. Am. Chem. Soc. 1989, 111, 391-393. (e) Parkin, G.; Bercaw, J. E. Polyhedron 1988, 1, 2053-2082. (f) Parkin, G.; Marsh, R. E.; Schaefer, W. P.; Bercaw, J. E. Inorg. Chem. 1988, 27, 3262-3264. (g) Silavwe, N. D.; Bruce, M. R. M.; Philbin, C. E.; Tyler, D. R. Inorg. Chem. 1988, 27, 4669-4676. (h) Silavwe, N. D.; Chiang, M. Y.; Tyler, D. R. Inorg. Chem. 1985, 24, 4219-4221. (i) Berry, M.; Davies, S. G.; Green, M. L. H. J. Chem. Soc., Chem. Commun. 1978, 99-100. (j) Green, M. L. H.; Lynch, A. H.; Swanwick, M. G. J. Chem. Soc., Dalton Trans. 1972, 1445-1447.
29. Group 6: (a) Henary, M.; Kaska, W. C.; Zink, J. I. Inorg. Chem. 1991, 30, 1674-1676. (b) Pilato, R. S.; Housmekerides, C. E.; Jernakoff, P.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1990, 9, 2333-2341. (c) Pilato, R. S.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Inorg. Chem. 1990, 29, 1986-1990. (d) Parkin, G.; Bercaw, J. E. J. Am. Chem. Soc. 1989, 111, 391-393. (e) Parkin, G.; Bercaw, J. E. Polyhedron 1988, 1, 2053-2082. (f) Parkin, G.; Marsh, R. E.; Schaefer, W. P.; Bercaw, J. E. Inorg. Chem. 1988, 27, 3262-3264. (g) Silavwe, N. D.; Bruce, M. R. M.; Philbin, C. E.; Tyler, D. R. Inorg. Chem. 1988, 27, 4669-4676. (h) Silavwe, N. D.; Chiang, M. Y.; Tyler, D. R. Inorg. Chem. 1985, 24, 4219-4221. (i) Berry, M.; Davies, S. G.; Green, M. L. H. J. Chem. Soc., Chem. Commun. 1978, 99-100. (j) Green, M. L. H.; Lynch, A. H.; Swanwick, M. G. J. Chem. Soc., Dalton Trans. 1972, 1445-1447.
30. Group 6: (a) Henary, M.; Kaska, W. C.; Zink, J. I. Inorg. Chem. 1991, 30, 1674-1676. (b) Pilato, R. S.; Housmekerides, C. E.; Jernakoff, P.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1990, 9, 2333-2341. (c) Pilato, R. S.; Rubin, D.; Geoffroy, G. L.; Rheingold, A. L. Inorg. Chem. 1990, 29, 1986-1990. (d) Parkin, G.; Bercaw, J. E. J. Am. Chem. Soc. 1989, 111, 391-393. (e) Parkin, G.; Bercaw, J. E. Polyhedron 1988, 1, 2053-2082. (f) Parkin, G.; Marsh, R. E.; Schaefer, W. P.; Bercaw, J. E. Inorg. Chem. 1988, 27, 3262-3264. (g) Silavwe, N. D.; Bruce, M. R. M.; Philbin, C. E.; Tyler, D. R. Inorg. Chem. 1988, 27, 4669-4676. (h) Silavwe, N. D.; Chiang, M. Y.; Tyler, D. R. Inorg. Chem. 1985, 24, 4219-4221. (i) Berry, M.; Davies, S. G.; Green, M. L. H. J. Chem. Soc., Chem. Commun. 1978, 99-100. (j) Green, M. L. H.; Lynch, A. H.; Swanwick, M. G. J. Chem. Soc., Dalton Trans. 1972, 1445-1447.
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80. (b) Minas da Piedade, M. E.; Shaofeng, L.; Pilcher, G. J. Chem. Thermodyn. 1987, 19, 195-202.
81. 2, M = Zr, Hf: (c) Schock, L. E.; Seyam, A. M.; Sabat, M.; Marks, T. J. Polyhedron 1988, 7, 1517-1529.
82. 2, M = Zr, Hf: (c) Schock, L. E.; Seyam, A. M.; Sabat, M.; Marks, T. J. Polyhedron 1988, 7, 1517-1529.
83. 2, M = Zr, Hf: (c) Schock, L. E.; Seyam, A. M.; Sabat, M.; Marks, T. J. Polyhedron 1988, 7, 1517-1529.
84. Nolan, S. P.; de la Vega, R. P.; Mukerjee, S. L.; Gonzalez, A. A.; Zhang, K.; Hoff, C. D. Polyhedron 1988, 16/17, 1491-1498. D(Mo-Cl) = 72.4 kcal/mol; D(Mo-I) = 51.8 kcal/mol.
85. 2 metallocene system.
86. (a) Walsh, R. Private communication to T.J.M.
87. (b) Becerra, R.; Walsh, R. In The Chemistry of Organosilicon Compounds; Rappaport, Z., Apeloig, Y., Eds.; in press.
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90. (c) Lanza, G.; Fragala, I. L.; Fu, P.-F.; Marks, T. J.; Wilson, D. C.; Rudolph, P. R. J. Am. Chem. Soc. Manuscript in preparation.
91. Prout, K.; Cameron, T. S.; Forder, R. A.; Critchiley, S. R.; Denton, B.; Rees, G. V. Acta Crystallogr. 1974, B30, 2290-2304.
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94. Evans, S.; Green, M. L. H.; Jewitt, A. F.; Orchard, A. F.; Pygall, C. F. J. Chem. Soc., Faraday Trans. 2 1972, 68, 1847-1865.
95. (a) Cauletti, C.; Clark, J. P.; Green, J. C.; Jackson, S. E.; Fragala, I.; Ciliberto, E.; Coleman, A. W. J. Electron Spectrosc. Relat. Phenom. 1980, 18, 61-73.
96. (b) Casarin, M.; Ciliberto, E.; Gulino, A.; Fragala, I. Organometallics 1989, 8, 900-906.
97. (c) Ciliberto, E.; Di Bella, S.; Gulino, A.; Fragala, I.; Petersen, J. L.; Marks, T. J. Organometallics 1992, 11, 1727-1737.
98. (d) Di Bella, S.; Gulino, A.; Lanza, G.; Fragala, G.; Marks, T. J. Organometallics 1993, 12, 3326-3332.
99. (e) Di Bella, S.; Gulino, A.; Lanza, G.; Fragala, I.; Stern, D.; Marks, T. J. Organometallics 1994, 13, 3810-3815.
100. (a) Kozlowski, P. M.; Davidson, E. R. Chem. Phys. Lett. 1994, 222, 615-620.
101. (b) Siegbahn, P. E.; Svensson, M. Chem. Phys. Lett. 1993, 216, 147-154.
102. (c) DiBella, S.; Lanza, G.; Gulino, A.; Fragala, I. Inorg. Chem. 1996, 35, 3885-3890.
103. 48b D(Re=O) was estimated to be 116.8(1.2) kcal/ mol.
104. (b) Gable, K. P.; Juliette, J. J.; Li, C.; Nolan, S. P. Organometallics 1996, 15, 5250-5251.
105. (a) Martinho Simoes, Ed. Energetics of Organometallic Species; Kluwer: Dordrecht, 1992; see also references therein.
106. (b) Hoff, C. D. Prog. Inorg. Chem. 1992, 40, 503-561.
107. (c) Marks, T. J., Ed. Bonding Energetics in Organometallic Compounds; ACS Symposium Series, American Chemical Society: Washington, DC, 1990; p 428.
108. (a) Metal-Ligand Bonding Energetics in Organotransition Metal Compounds; Marks, T. J., Ed.; Polyhedron Symposium-in-Print; 1988; Vol. 7.
109. (b) Skinner, H. A.; Connor, J. A. Pure Appl. Chem. 1985, 57, 79-88
110. (c) Pilcher, G.; Skinner, H. A. In The Chemistry of the Metal-Carbon-Bond; Harley, F. R., Patai, S., Eds; Wiley: New York, 1982; pp 43-90.
111. King, W. A.; Arney, D. S. J.; Burns, C. J.; Marks, T. J. Unpublished results.
112. Pedley, J. B.; Marshall, E. M. J. Phys. Chem. Ref. Data 1984, 12, 967-971.
113. 3)=D(Mo-ligand)/D(W-ligand) proportionality is employed. It is assumed that metal substituent effects on bond enthalpies attenuate in two bonds.
114. (a) Organic molecules: Isaacs, N. S. Physical Organic Chemistry; Wiley: New York, 1987; pp 282-291. (b) Metallacyclobutanes: Bruno, J. W.; Marks, T. J.; Morss, L. R. J. Am. Chem. Soc. 1983, 105, 6824-6832.
115. (a) Organic molecules: Isaacs, N. S. Physical Organic Chemistry; Wiley: New York, 1987; pp 282-291. (b) Metallacyclobutanes: Bruno, J. W.; Marks, T. J.; Morss, L. R. J. Am. Chem. Soc. 1983, 105, 6824-6832.
116. (a) Griller, D.; Kanabus-Kaminska, J. M.; Maccoll, A. J. Mol. Struct. 1988, 163, 125-131.
117. (b) Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd ed.; Chapman and Hall: London, 1986; Appendix Tables 1 and 3.
118. (c) McMillan, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493-532 and references therein.
119. (d) Benson, S. W. Thermochemical Kinetics, 2nd ed.; John Wiley and Sons: New York, 1976; Appendix Tables A.10, A.11, and A.22.
120. (d) Benson, S. W. J. Chem. Educ. 1965, 42, 502-518.
121. For non-metallocene examples where this pathway is thought to be operative, see: (a) Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425-426 and references therein. (b) Fu, H.; Look, G. C.; Zhang, W.; Jacobsen, E. N.; Wong, C.-H. J. Org. Chem. 1991, 56, 6497-6502. (c) Groves, J. T.; Stern, M. K. J. Am. Chem. Soc. 1988, 110, 8628-8638.
122. For non-metallocene examples where this pathway is thought to be operative, see: (a) Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425-426 and references therein. (b) Fu, H.; Look, G. C.; Zhang, W.; Jacobsen, E. N.; Wong, C.-H. J. Org. Chem. 1991, 56, 6497-6502. (c) Groves, J. T.; Stern, M. K. J. Am. Chem. Soc. 1988, 110, 8628-8638.
123. For non-metallocene examples where this pathway is thought to be operative, see: (a) Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425-426 and references therein. (b) Fu, H.; Look, G. C.; Zhang, W.; Jacobsen, E. N.; Wong, C.-H. J. Org. Chem. 1991, 56, 6497-6502. (c) Groves, J. T.; Stern, M. K. J. Am. Chem. Soc. 1988, 110, 8628-8638.
124. (a) Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
125. (b) Sundermeyer, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1144-1146.
126. (c) Jorgensen, K. A.; Schiott, B. Chem. Rev. 1990, 90, 1483-1506.
127. (d) Mimoun, H. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxford, 1987; Chapter 61.3.
128. The adverse TΔ5 contribution to ΔG under these conditions is likely on the order of ∼4-8 kcal/mol owing to loss of translational and rotational entropy: (a) Smith, G. M.; Carpenter, J. D.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 6805-6807. (b) Menger, F. M.; Venkataram, U. V. J. Am. Chem. Soc. 1985, 107, 4706-4709 and references therein. (c) Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: New York, 1984; pp 1-54. (d) Kirby, A. Adv. Phys. Org. Chem. 1980, 17, 183-278.
129. The adverse TΔ5 contribution to ΔG under these conditions is likely on the order of ∼4-8 kcal/mol owing to loss of translational and rotational entropy: (a) Smith, G. M.; Carpenter, J. D.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 6805-6807. (b) Menger, F. M.; Venkataram, U. V. J. Am. Chem. Soc. 1985, 107, 4706-4709 and references therein. (c) Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: New York, 1984; pp 1-54. (d) Kirby, A. Adv. Phys. Org. Chem. 1980, 17, 183-278.
130. The adverse TΔ5 contribution to ΔG under these conditions is likely on the order of ∼4-8 kcal/mol owing to loss of translational and rotational entropy: (a) Smith, G. M.; Carpenter, J. D.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 6805-6807. (b) Menger, F. M.; Venkataram, U. V. J. Am. Chem. Soc. 1985, 107, 4706-4709 and references therein. (c) Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: New York, 1984; pp 1-54. (d) Kirby, A. Adv. Phys. Org. Chem. 1980, 17, 183-278.
131. The adverse TΔ5 contribution to ΔG under these conditions is likely on the order of ∼4-8 kcal/mol owing to loss of translational and rotational entropy: (a) Smith, G. M.; Carpenter, J. D.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 6805-6807. (b) Menger, F. M.; Venkataram, U. V. J. Am. Chem. Soc. 1985, 107, 4706-4709 and references therein. (c) Page, M. I. In The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: New York, 1984; pp 1-54. (d) Kirby, A. Adv. Phys. Org. Chem. 1980, 17, 183-278.
132. calcd vales of -23 (M = Mo) and -27 (M = W) kcal/ mol for formation of such an oxametallacycle: (Matrix Presented) This reflects the generally greater exothermicity of additions to allenes.
133. (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295-9306.
134. (b) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770-3772.
135. (c) Li, Y.; Fu, P.-F.; Marks, T. J. Organometallics 1994, 13, 439-440.
136. Moro-Oka, Y.; Ueda, W. Adv. Catal. 1994, 40, 233-273.
137. 6e