Metathesis Activity Encoded in the Metallacyclobutane Carbon-13 NMR Chemical Shift Tensors

ACS Central Science

Volumn 3, Issue 7, 2017, Pages 759-768

  Gordon, Christopher P ^a   Yamamoto, Keishi ^a   Liao, Wei Chih ^a   Allouche, Florian ^a   Andersen, Richard A ^b   Copéret, Christophe ^a   Raynaud, Christophe ^c   Eisenstein, Odile ^c,d  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITÉ DE MONTPELLIER   (France)

^d UNIVERSITY OF OSLO   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

BOND LENGTH; CARBON; CHEMICAL ANALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; ORGANOMETALLICS; PRECIOUS METAL COMPOUNDS; PRINCIPAL COMPONENT ANALYSIS; REFRACTORY METAL COMPOUNDS; TENSORS; TRANSITION METALS;

CHEMICAL AND PHYSICAL PROPERTIES; CHEMICAL SHIFT TENSORS; METATHESIS ACTIVITY; OLEFIN METATHESIS; ORGANOMETALLIC INTERMEDIATES; PREDICTIVE VALUES; PRINCIPAL COMPONENTS; SOLID STATE NMR;

CHEMICAL SHIFT;

EID: 85026360915     PISSN: 23747943     EISSN: 23747951     Source Type: Journal    
DOI: 10.1021/acscentsci.7b00174     Document Type: Article

References (109)

1. Grubbs, R. H.; Chang, S. Recent Advances in Olefin Metathesis and its Application in Organic Synthesis Tetrahedron 1998, 54, 4413-4450 10.1016/S0040-4020(97)10427-6
2. Fürstner, A. Olefin Metathesis and Beyond Angew. Chem., Int. Ed. 2000, 39, 3012-3043 10.1002/1521-3773(20000901)39:17<3012::AID-ANIE3012>3.0.CO;2-G
3. Schrock, R. R. High Oxidation State Multiple Metal-Carbon Bonds Chem. Rev. 2002, 102, 145-180 10.1021/cr0103726
4. Hoveyda, A. H.; Zhugralin, A. R. The Remarkable Metal-Catalysed Olefin Metathesis Reaction Nature 2007, 450, 243-251 10.1038/nature06351
5. Fürstner, A. Metathesis in Total Synthesis Chem. Commun. 2011, 47, 6505-6511 10.1039/c1cc10464k
6. Grela, K. Olefin Metathesis: Theory and Practice; Wiley VCH: Weinheim, 2014.
7. Grubbs, R. H.; Wenzel, A. G.; O'Leary, D. J.; Khosravi, E. Handbook of Metathesis, 3 Vol. Set, 2 nd ed.; Wiley VCH: Weinheim, 2015.
8. Higman, C. S.; Lummiss, J. A. M.; Fogg, D. E. Olefin Metathesis at the Dawn of Implementation in Pharmaceutical and Specialty-Chemicals Manufacturing Angew. Chem., Int. Ed. 2016, 55, 3552-3565 10.1002/anie.201506846
9. Hérisson, P. J.-L.; Chauvin, Y. Catalyse de Transformation des Oléfines par les Complexes Du Tungstène. II. Télomérisation des Oléfines Cycliques en Présence d'Oléfines Acycliques Makromol. Chem. 1971, 141, 161-176 10.1002/macp.1971.021410112
10. Chauvin, Y. Olefin Metathesis: The Early Days (Nobel Lecture) Angew. Chem., Int. Ed. 2006, 45, 3740-3747 10.1002/anie.200601234
11. 0 Re-Based Olefin Metathesis Catalysts, Re(≡CR)(=CHR)(X)(Y): The Key Role of X and Y Ligands for Efficient Active Sites J. Am. Chem. Soc. 2005, 127, 14015-14025 10.1021/ja053528i
12. 0-Olefin Metathesis Catalysts: Which Metal, Which Ligands? J. Am. Chem. Soc. 2007, 129, 8207-8216 10.1021/ja070625y
13. Leduc, A.-M.; Salameh, A.; Soulivong, D.; Chabanas, M.; Basset, J.-M.; Copéret, C.; Solans-Monfort, X.; Clot, E.; Eisenstein, O.; Böhm, V. P. W.; Röper, M. β-H Transfer from the Metallacyclobutane: A Key Step in the Deactivation and Byproduct Formation for the Well-Defined Silica-Supported Rhenium Alkylidene Alkene Metathesis Catalyst J. Am. Chem. Soc. 2008, 130, 6288-6297 10.1021/ja800189a
14. 4 Alkene Metathesis Catalysts from DFT Calculations J. Am. Chem. Soc. 2010, 132, 7750-7757 10.1021/ja101597s
15. 0-Metal Species: How and why do they Differ in Structure, Activity, and Efficiency in Alkene Metathesis? Organometallics 2012, 31, 6812-6822 10.1021/om300576r
16. 0 Metal Alkylidene Catalysts: Structural Preferences and Consequences in Alkene Metathesis Organometallics 2015, 34, 1668-1680 10.1021/acs.organomet.5b00147
17. 0" Alkylidene and Metallacyclobutane Complexes. In Prog. Inorg. Chem.; John Wiley & Sons, Inc., 1991; pp 1-74.
18. Schrock, R. R.; Hoveyda, A. H. Molybdenum and Tungsten Imido Alkylidene Complexes as Efficient Olefin-Metathesis Catalysts Angew. Chem., Int. Ed. 2003, 42, 4592-4633 10.1002/anie.200300576
19. Schrock, R. R. Multiple Metal-Carbon Bonds for Catalytic Metathesis Reactions (Nobel Lecture) Angew. Chem., Int. Ed. 2006, 45, 3748-3759 10.1002/anie.200600085
20. Schrock, R. R. Recent Advances in High Oxidation State Mo and W Imido Alkylidene Chemistry Chem. Rev. 2009, 109, 3211-3226 10.1021/cr800502p
21. Wallace, K. C.; Dewan, J. C.; Schrock, R. R. Multiple Metal-Carbon Bonds. 44. Isolation and Characterization of the First Simple Tantalacyclobutane Complexes Organometallics 1986, 5, 2162-2164 10.1021/om00141a045
22. Wallace, K. C.; Liu, A. H.; Dewan, J. C.; Schrock, R. R. Preparation and Reactions of Tantalum Alkylidene Complexes Containing Bulky Phenoxide or Thiolate Ligands. Controlling Ring-Opening Metathesis Polymerization Activity and Mechanism through Choice of Anionic Ligand J. Am. Chem. Soc. 1988, 110, 4964-4977 10.1021/ja00223a014
23. 2 (M = W, Mo) with Methyl Acrylate and N,N-Dimethylacrylamide to Give Metallacyclobutane Complexes Organometallics 1989, 8, 2260-2265 10.1021/om00111a025
24. Marinescu, S. C.; Schrock, R. R.; Müller, P.; Hoveyda, A. H. Ethenolysis Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide (MAP) Complexes of Molybdenum J. Am. Chem. Soc. 2009, 131, 10840-10841 10.1021/ja904786y
25. 2) J. Am. Chem. Soc. 1987, 109, 4282-4291 10.1021/ja00248a024
26. 2 and Related Tungstacyclobutane Complexes. Controlling Metathesis Activity through the Choice of Alkoxide Ligand J. Am. Chem. Soc. 1988, 110, 1423-1435 10.1021/ja00213a014
27. 2 Organometallics 1989, 8, 2266-2268 10.1021/om00111a026
28. Schrock, R. R.; DePue, R. T.; Feldman, J.; Yap, K. B.; Yang, D. C.; Davis, W. M.; Park, L.; DiMare, M.; Schofield, M. Further Studies of Imido Alkylidene Complexes of Tungsten, Well-Characterized Olefin Metathesis Catalysts with Controllable Activity Organometallics 1990, 9, 2262-2275 10.1021/om00158a025
29. Feldman, J.; Davis, W. M.; Thomas, J. K.; Schrock, R. R. Preparation and Reactivity of Tungsten(VI) Metallacyclobutane Complexes. Square Pyramids Versus Trigonal Bipyramids Organometallics 1990, 9, 2535-2548 10.1021/om00159a024
30. 2 J. Am. Chem. Soc. 1993, 115, 2980-2981 10.1021/ja00060a058
31. Copéret, C.; Chabanas, M.; Petroff Saint-Arroman, R.; Basset, J.-M. Homogeneous and Heterogeneous Catalysis: Bridging the Gap through Surface Organometallic Chemistry Angew. Chem., Int. Ed. 2003, 42, 156-181 10.1002/anie.200390072
32. Copéret, C. Design and Understanding of Heterogeneous Alkene Metathesis Catalysts Dalton Trans. 2007, 5498-5504 10.1039/b713314f
33. Copéret, C.; Comas-Vives, A.; Conley, M. P.; Estes, D. P.; Fedorov, A.; Mougel, V.; Nagae, H.; Núñez-Zarur, F.; Zhizhko, P. A. Surface Organometallic and Coordination Chemistry toward Single-Site Heterogeneous Catalysts: Strategies, Methods, Structures, and Activities Chem. Rev. 2016, 116, 323-421 10.1021/acs.chemrev.5b00373
34. Blanc, F.; Berthoud, R.; Copéret, C.; Lesage, A.; Emsley, L.; Singh, R.; Kreickmann, T.; Schrock, R. R. Direct Observation of Reaction Intermediates for a Well Defined Heterogeneous Alkene Metathesis Catalyst Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 12123-12127 10.1073/pnas.0802147105
35. 0 Silica Supported (≡SiO)W(NAr)(=CHtBu) (OR) Catalysts Chem. Sci. 2014, 5, 2475-2481 10.1039/c4sc00230j
36. Conley, M. P.; Forrest, W. P.; Mougel, V.; Copéret, C.; Schrock, R. R. Bulky Aryloxide Ligand Stabilizes a Heterogeneous Metathesis Catalyst Angew. Chem., Int. Ed. 2014, 53, 14221-14224 10.1002/anie.201408880
37. Mougel, V.; Santiago, C. B.; Zhizhko, P. A.; Bess, E. N.; Varga, J.; Frater, G.; Sigman, M. S.; Copéret, C. Quantitatively Analyzing Metathesis Catalyst Activity and Structural Features in Silica-Supported Tungsten Imido-Alkylidene Complexes J. Am. Chem. Soc. 2015, 137, 6699-6704 10.1021/jacs.5b03344
38. Mougel, V.; Chan, K.-W.; Siddiqi, G.; Kawakita, K.; Nagae, H.; Tsurugi, H.; Mashima, K.; Safonova, O.; Copéret, C. Low Temperature Activation of Supported Metathesis Catalysts by Organosilicon Reducing Agents ACS Cent. Sci. 2016, 2, 569-576 10.1021/acscentsci.6b00176
39. Ong, T.-C.; Liao, W.-C.; Mougel, V.; Gajan, D.; Lesage, A.; Emsley, L.; Copéret, C. Atomistic Description of Reaction Intermediates for Supported Metathesis Catalysts Enabled by DNP SENS Angew. Chem., Int. Ed. 2016, 55, 4743-4747 10.1002/anie.201510821
40. Mougel, V.; Pucino, M.; Copéret, C. Strongly σ Donating Thiophenoxide in Silica-Supported Tungsten Oxo Catalysts for Improved 1-Alkene Metathesis Efficiency Organometallics 2015, 34, 551-554 10.1021/om5013105
41. Allouche, F.; Mougel, V.; Copéret, C. Activating Thiolate-Based Imidoalkylidene Tungsten(VI) Metathesis Catalysts by Grafting onto Silica Asian J. Org. Chem. 2015, 4, 528-532 10.1002/ajoc.201500038
42. 3 Olefin Metathesis Catalysts J. Am. Chem. Soc. 2016, 138, 6774-6785 10.1021/jacs.6b00447
43. Romero, P. E.; Piers, W. E. Direct Observation of a 14-Electron Ruthenacyclobutane Relevant to Olefin Metathesis J. Am. Chem. Soc. 2005, 127, 5032-5033 10.1021/ja042259d
44. Wenzel, A. G.; Grubbs, R. H. Ruthenium Metallacycles Derived from 14-Electron Complexes. New Insights into Olefin Metathesis Intermediates J. Am. Chem. Soc. 2006, 128, 16048-16049 10.1021/ja0666598
45. van der Eide, E. F.; Romero, P. E.; Piers, W. E. Generation and Spectroscopic Characterization of Ruthenacyclobutane and Ruthenium Olefin Carbene Intermediates Relevant to Ring Closing Metathesis Catalysis J. Am. Chem. Soc. 2008, 130, 4485-4491 10.1021/ja710364e
46. Cavallo, L. Mechanism of Ruthenium-Catalyzed Olefin Metathesis Reactions from a Theoretical Perspective J. Am. Chem. Soc. 2002, 124, 8965-8973 10.1021/ja016772s
47. Adlhart, C.; Chen, P. Mechanism and Activity of Ruthenium Olefin Metathesis Catalysts: The Role of Ligands and Substrates from a Theoretical Perspective J. Am. Chem. Soc. 2004, 126, 3496-3510 10.1021/ja0305757
48. Occhipinti, G.; Bjørsvik, H.-R.; Jensen, V. R. Quantitative Structure-Activity Relationships of Ruthenium Catalysts for Olefin Metathesis J. Am. Chem. Soc. 2006, 128, 6952-6964 10.1021/ja060832i
49. Webster, C. E. Computational Insights into Degenerate Ethylene Exchange with a Grubbs-Type Catalyst J. Am. Chem. Soc. 2007, 129, 7490-7491 10.1021/ja071588d
50. Poater, A.; Ragone, F.; Correa, A.; Szadkowska, A.; Barbasiewicz, M.; Grela, K.; Cavallo, L. Mechanistic Insights into the Cis-Trans Isomerization of Ruthenium Complexes Relevant to Catalysis of Olefin Metathesis Chem.-Eur. J. 2010, 16, 14354-14364 10.1002/chem.201001849
51. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. Olefin Homologation with Titanium Methylene Compounds J. Am. Chem. Soc. 1978, 100, 3611-3613 10.1021/ja00479a061
52. Howard, T. R.; Lee, J. B.; Grubbs, R. H. Titanium Metallacarbene-Metallacyclobutane Reactions: Stepwise Metathesis J. Am. Chem. Soc. 1980, 102, 6876-6878 10.1021/ja00542a050
53. Eisenstein, O.; Hoffmann, R.; Rossi, A. R. Some Geometrical and Electronic Features of the Intermediate Stages of Olefin Metathesis J. Am. Chem. Soc. 1981, 103, 5582-5584 10.1021/ja00408a057
54. Dedieu, A.; Eisenstein, O. Metallacyclobutanes: Are They Distorted? A Theoretical Ab-Inito Study Nouv. J. Chim. 1982, 6, 337-340
55. Gilliom, L. R.; Grubbs, R. H. Titanacyclobutanes Derived from Strained, Cyclic Olefins: The Living Polymerization of Norbornene J. Am. Chem. Soc. 1986, 108, 733-742 10.1021/ja00264a027
56. Straus, D. A.; Grubbs, R. H. Titanacyclobutanes: Substitution Pattern and Stability Organometallics 1982, 1, 1658-1661 10.1021/om00072a020
57. Scheins, S.; Messerschmidt, M.; Gembicky, M.; Pitak, M.; Volkov, A.; Coppens, P.; Harvey, B. G.; Turpin, G. C.; Arif, A. M.; Ernst, R. D. Charge Density Analysis of the (C-C)→Ti Agostic Interactions in a Titanacyclobutane Complex J. Am. Chem. Soc. 2009, 131, 6154-6160 10.1021/ja807649k
58. Seetz, J. W. F. L.; Schat, G.; Akkerman, O. S.; Bickelhaupt, F. Zircona- and Hafnacyclobutenes-a New Route to Metallacyclobutanes Angew. Chem., Int. Ed. Engl. 1983, 22, 248-249 10.1002/anie.198302481
59. Ephritikhine, M.; Francis, B. R.; Green, M. L. H.; Mackenzie, R. E.; Smith, M. J. Bis(η-Cyclopentadienyl)-Molybdenum and -Tungsten Chemistry: σ- and η-Allylic and Metallacyclobutane Derivatives J. Chem. Soc., Dalton Trans. 1977, 1131-1135 10.1039/DT9770001131
60. Harvey, B. G.; Mayne, C. L.; Arif, A. M.; Ernst, R. D. Structural and Spectroscopic Demonstration of Agostic C-C Interactions in Electron-Deficient Metallacyclobutanes and Related Cage Complexes: Possible Implications for Olefin Polymerizations and Metatheses J. Am. Chem. Soc. 2005, 127, 16426-16435 10.1021/ja052287b
61. Andersen, R. A.; Jones, R. A.; Wilkinson, G. Trimethylsilylmethyl and Other Alkyls of Chromium, Molybdenum, Ruthenium, and Rhodium from Interaction of Magnesium Dialkyls with Metal-Metal Bonded Binuclear Acetates of Chromium(II), Molybdenum(II), Ruthenium(II, III), and Rhodium(II) J. Chem. Soc., Dalton Trans. 1978, 446-453 10.1039/DT9780000446
62. McNeill, K.; Andersen, R. A.; Bergman, R. G. C-C and C-H Bond Activation at Ruthenium(II): The Stepwise Degradation of a Neopentyl Ligand to a Trimethylenemethane Ligand J. Am. Chem. Soc. 1997, 119, 11244-11254 10.1021/ja972131e
63. 2-Olefin-Komplexen Und Vier- bis Sechsgliedrigen Metallacycloalkanen Von Ruthenium und Osmium Chem. Ber. 1989, 122, 1403-1409 10.1002/cber.19891220804
64. 2,P)-rhodium J. Chem. Soc., Chem. Commun. 1982, 945-946 10.1039/C39820000945
65. Tulip, T. H.; Thorn, D. L. Hydridometallacycloalkane Complexes of Iridium. Unassisted Intramolecular Distal Carbon-Hydrogen Bond Activation J. Am. Chem. Soc. 1981, 103, 2448-2450 10.1021/ja00399a069
66. Adams, D. M.; Chatt, J.; Guy, R. G.; Sheppard, N. The Structure of ″Cyclopropane Platinous Chloride″ J. Chem. Soc. 1961, 0, 738-742 10.1039/JR9610000738
67. Puddephatt, R. J. Platinacyclobutane Chemistry Coord. Chem. Rev. 1980, 33, 149-194 10.1016/S0010-8545(00)80406-3
68. Jennings, P. W.; Johnson, L. L. Metallacyclobutane Complexes of the Group Eight Transition Metals: Synthesis, Characterizations, and Chemistry Chem. Rev. 1994, 94, 2241-2290 10.1021/cr00032a003
69. Widdifield, C. M.; Schurko, R. W. Understanding Chemical Shielding Tensors Using Group Theory, MO Analysis, and Modern Density-Functional Theory Concepts Magn. Reson., Part A 2009, 34A, 91-123 10.1002/cmr.a.20136
70. 0 Olefin Metathesis Catalysts J. Am. Chem. Soc. 2016, 138, 2261-2272 10.1021/jacs.5b12597
71. Yamamoto, K.; Gordon, C. P.; Liao, W.-C.; Copéret, C.; Raynaud, C.; Eisenstein, O. Orbital Analysis of Carbon-13 Chemical Shift Tensors Reveals Patterns to Distinguish Fischer and Schrock Carbenes. Angew. Chem., Int. Ed. 2017, DOI: 10.1002/anie.201701537
72. Herzfeld, J.; Berger, A. E. Sideband Intensities in NMR Spectra of Samples Spinning at the Magic Angle J. Chem. Phys. 1980, 73, 6021-6030 10.1063/1.440136
73. Bohmann, J. A.; Weinhold, F.; Farrar, T. C. Natural Chemical Shielding Analysis of Nuclear Magnetic Resonance Shielding Tensors from Gauge-Including Atomic Orbital Calculations J. Chem. Phys. 1997, 107, 1173-1184 10.1063/1.474464
74. Autschbach, J. Analyzing NMR Shielding Tensors Calculated with Two-Component Relativistic Methods Using Spin-Free Localized Molecular Orbitals J. Chem. Phys. 2008, 128, 164112 10.1063/1.2905235
75. Autschbach, J.; Zheng, S. Analyzing Pt Chemical Shifts Calculated from Relativistic Density Functional Theory Using Localized Orbitals: The Role of Pt 5d Lone Pairs Magn. Reson. Chem. 2008, 46, S45-S55 10.1002/mrc.2289
76. Aquino, F.; Pritchard, B.; Autschbach, J. Scalar Relativistic Computations and Localized Orbital Analyses of Nuclear Hyperfine Coupling and Paramagnetic NMR Chemical Shifts J. Chem. Theory Comput. 2012, 8, 598-609 10.1021/ct2008507
77. 1H NMR Chemical Shift in Low-Valent Transition-Metal Hydrides Organometallics 1996, 15, 3920-3923 10.1021/om960218n
78. 31P Chemical Shielding Tensors in Terminal Phosphido Complexes Containing a Phosphorus-Metal Triple Bond J. Am. Chem. Soc. 1996, 118, 10654-10655 10.1021/ja960639w
79. 17O NMR Shielding Tensors in Transition Metal Carbonyls Based on Density Functional Theory and Gauge-Including Atomic Orbitals J. Phys. Chem. 1996, 100, 3359-3367 10.1021/jp952007m
80. Wiberg, K. B.; Hammer, J. D.; Zilm, K. W.; Cheeseman, J. R. NMR Chemical Shifts. 3. A Comparison of Acetylene, Allene, and the Higher Cumulenes J. Org. Chem. 1999, 64, 6394-6400 10.1021/jo990423n
81. 29Si Chemical Shifts and Bonding in Disilenes. A Quantum Chemical Analysis Organometallics 2003, 22, 2442-2449 10.1021/om030101g
82. 29Si NMR Chemical Shifts in Heteroatom-Substituted Silyllithium Compounds: A Quantum-Chemical Analysis Organometallics 2004, 23, 3647-3655 10.1021/om049812k
83. 15N NMR in Combination with DFT Calculations Polyhedron 2004, 23, 2751-2768 10.1016/j.poly.2004.08.010
84. 29Si NMR Chemical Shifts in RSi≡SiR Organometallics 2005, 24, 6319-6330 10.1021/om058033g
85. 29Si NMR Study of RSiSiR: A Tool for Analyzing the Nature of the Si-Si Bond J. Am. Chem. Soc. 2006, 128, 14472-14473 10.1021/ja065817s
86. Rossini, A. J.; Mills, R. W.; Briscoe, G. A.; Norton, E. L.; Geier, S. J.; Hung, I.; Zheng, S.; Autschbach, J.; Schurko, R. W. Solid-State Chlorine NMR of Group IV Transition Metal Organometallic Complexes J. Am. Chem. Soc. 2009, 131, 3317-3330 10.1021/ja808390a
87. Epping, J. D.; Yao, S.; Karni, M.; Apeloig, Y.; Driess, M. Si=X Multiple Bonding with Four-Coordinate Silicon? Insights into the Nature of the Si=O and Si=S Double Bonds in Stable Silanoic Esters and Related Thioesters: A Combined NMR Spectroscopic and Computational Study J. Am. Chem. Soc. 2010, 132, 5443-5455 10.1021/ja1004812
88. 15N NMR Chemical Shifts in 6-Substituted Purines Phys. Chem. Chem. Phys. 2011, 13, 15854-15864 10.1039/c1cp20680j
89. 17O NMR and Computational Studies of Terminal Transition Metal Oxo Compounds Chem. Sci. 2012, 3, 391-397 10.1039/C1SC00725D
90. 13C NMR Chemical Shift of Methoxy Groups in Aromatic Natural Compounds J. Phys. Chem. A 2013, 117, 661-669 10.1021/jp310470f
91. 17O NMR Chemical Shifts in Oxometalates: From the Simplest Monometallic Species to Mixed-Metal Polyoxometalates Chem. Sci. 2014, 5, 2031-2042 10.1039/c4sc00083h
92. Vícha, J.; Straka, M.; Munzarová, M. L.; Marek, R. Mechanism of Spin-Orbit Effects on the Ligand NMR Chemical Shift in Transition-Metal Complexes: Linking NMR to EPR J. Chem. Theory Comput. 2014, 10, 1489-1499 10.1021/ct400726y
93. 31P NMR Chemical Shifts in Polyoxometalates Phys. Chem. Chem. Phys. 2015, 17, 8723-8731 10.1039/C4CP05016A
94. Vummaleti, S. V. C.; Nelson, D. J.; Poater, A.; Gomez-Suarez, A.; Cordes, D. B.; Slawin, A. M. Z.; Nolan, S. P.; Cavallo, L. What Can NMR Spectroscopy of Selenoureas and Phosphinidenes Teach Us About the π-Accepting Abilities of N-Heterocyclic Carbenes? Chem. Sci. 2015, 6, 1895-1904 10.1039/C4SC03264K
95. Lummiss, J. A. M.; Perras, F. A.; McDonald, R.; Bryce, D. L.; Fogg, D. E. Sterically Driven Olefin Metathesis: The Impact of Alkylidene Substitution on Catalyst Activity Organometallics 2016, 35, 691-698 10.1021/acs.organomet.5b00984
96. + Congeners Dalton Trans. 2017, 46, 2861-2873 10.1039/C7DT00117G
97. Greif, A. H.; Hrobarik, P.; Kaupp, M. Insights into Trans-Ligand and Spin-Orbit Effects on Electronic Structure and Ligand NMR Shifts in Transition-Metal Complexes Chem.-Eur. J. 2017, 10.1002/chem.201700844
98. Gessner, V. H.; Meier, F.; Uhrich, D.; Kaupp, M. Synthesis and Bonding in Carbene Complexes of an Unsymmetrical Dilithio Methandiide: A Combined Experimental and Theoretical Study Chem.-Eur. J. 2013, 19, 16729-16739 10.1002/chem.201303115
99. Suresh, C. H.; Baik, M.-H. α,β-(C-C-C) Agostic Bonds in Transition Metal Based Olefin Metathesis Catalyses Dalton Trans. 2005, 18, 2982-2984 10.1039/b508192k
100. Etienne, M.; Weller, A. S. Intramolecular C-C Agostic Complexes: C-C Sigma Interactions by Another Name Chem. Soc. Rev. 2014, 43, 242-259 10.1039/C3CS60295H
101. n Complexes J. Am. Chem. Soc. 1976, 98, 1729-1742 10.1021/ja00423a017
102. Albright, T. A.; Burdett, J. K.; Whangbo, M.-H. Orbital Interactions in Chemistry. 2 nd ed.; Wiley VCH: Weinheim, 2013.
103. +, and HC≡CF J. Phys. Chem. A 1998, 102, 8766-8773 10.1021/jp982214x
104. Arduengo, A. J.; Dixon, D. A.; Kumashiro, K. K.; Lee, C.; Power, W. P.; Zilm, K. W. Chemical Shielding Tensor of a Carbene J. Am. Chem. Soc. 1994, 116, 6361-6367 10.1021/ja00093a041
105. 3 J. Am. Chem. Soc. 1993, 115, 636-646 10.1021/ja00055a037
106. 3) Complexes Dalton Trans. 2002, 534-539 10.1039/b107698c
107. Hoffmann, R. Building Bridges between Inorganic and Organic Chemistry (Nobel Lecture) Angew. Chem., Int. Ed. Engl. 1982, 21, 711-724 10.1002/anie.198207113
108. van de Heisteeg, B. J. J.; Schat, G.; Akkerman, O. S.; Bickelhaupt, F. Synthese von 1,3-Dimetallacyclobutanen mit dem Methylen-di-Grignardreagens J. Organomet. Chem. 1986, 308, 1-10 10.1016/S0022-328X(00)99515-9
109. Van de Heisteeg, B. J. J.; Schat, G.; Akkerman, O. S.; Bickelhaupt, F. Synthesis of 1,3-Metallatitanacyclobutanes of Group 4 Organometallics 1985, 4, 1141-1142 10.1021/om00125a037