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	Contents


	Preface to the Third Edition	V
	Preface to the First Edition	VII
	Introduction
1	Milestones in Organometallic Chemistry	3
2	Organoelement Compounds: Classification and Electronegativity Considerations	11
3	Energy, Polarity, and Reactivity of the M–C Bond	15
3.1	Stability of Main-Group Organometallic Compounds	15
3.2	Lability of Main-Group Organometallic Compounds	17
	Excursion 1: Where does our knowledge of M–C bond energies come from?	19
	Main-Group Organometallics
4	Overview of Preparation Methods	27
5	Organometallic Chemistry of Alkali Metals (Group 1)	33
5.1	Organolithium Compounds	33
	Excursion 2: ⁶Li and ⁷Li NMR Spectroscopy of Organolithium Compounds	39
5.2	Organometallic Compounds of the Heavier Alkali Metals	50
	Excursion 3: EPR Spectroscopy of Organoalkali-Metal Compounds	55
6	Organometallic Compounds of Groups 2 and 12	59
6.1	Organometallic Compounds of the Alkaline-Earth Metals (Group 2)	59
6.1.1	Organoberyllium Compounds	59
6.1.2	Organomagnesium Compounds	62
6.1.3	Organocalcium, -strontium, and -barium Compounds	70
6.2	Organometallic Compounds of Zn, Cd, Hg (Group 12)	73
6.2.1	Organozinc Compounds	73
6.2.2	Organocadmium Compounds	77
6.2.3	Organomercury Compounds	78
	Excursion 4: Organomercury Compounds in vivo	82
7	Organometallic Compounds of the Boron Group (Group 13)	87
7.1	Organoboron Compounds	87
7.1.1	Organoboranes	87
7.1.2	Organoboron–Transition-Metal Compounds	93
7.1.3	Boron Heterocycles	94
7.1.4	Polyhedral Boranes, Carbaboranes, and Heterocarbaboranes	99
	Excursion 5: ¹¹B NMR Spectroscopy of Organoboron Compounds	108
7.2	Organoaluminum Compounds	110
7.2.1	Organoaluminum^III Compounds	111
7.2.2	Subvalent Organoaluminum Compounds	123
7.3	Gallium, Indium, and Thallium Organyls	126
7.3.1	Ga^III, In^III, and Tl^III Organyls and their Lewis Base Adducts	126
7.3.2	Ga^II,I, In^II,I, and Tl^II,I Organyls	129
7.3.3	Thallium in Organic Synthesis	136
8	Organoelement Compounds of the Carbon Group (Group 14)	139
8.1	Organosilicon Compounds	142
8.1.1	Silicon Organyls of Coordination Number 4	142
8.1.2	Organosilicon Compounds with Coordination Numbers 3, 2, and 1 and Their Subsequent Products	153
8.2	Organogermanium Compounds	171
8.2.1	Germanium Organyls of Coordination Number 4	171
8.2.2	Organogermanium Compounds with Coordination Numbers 3, 2, and 1 and Their Subsequent Products	175
8.3	Organotin Compounds	179
	Excursion 6: ¹¹⁹Sn Mössbauer and ¹¹⁹Sn NMR Spectroscopy	179
8.3.1	Organotin Compounds with Coordination Numbers 6, 5, and 4 and Their Subsequent Products	182
8.3.2	Organotin Compounds with Coordination Numbers 3, 2, and 1 and Their Subsequent Products	191
8.4	Organolead Compounds	198
8.4.1	Pb^IV Organyls	199
8.4.2	Pb^III, Pb^II, and Pb^I Organyls	203
9	Organoelement Compounds of the Nitrogen Group (Group 15)	211
9.1	E^V Organyls (E = As, Sb, Bi)	212
9.1.1	Pentaorganoelement Compounds R₅E	212
9.1.2	Organoelement Derivatives RnEX_5–n	215
9.2	E^III Organyls (E = As, Sb, Bi)	217
9.2.1	Trisorganoelement Compounds R₃E	218
9.2.2	Organoelement Derivatives R_nEX_3–n	221
9.3	Chains and Rings Containing E–E Single Bonds	224
9.4	E (P, As, Sb, Bi) as Partners in Multiple Bonds	229
9.4.1	E=C(p–p) Bonds	229
9.4.2	EC(p–p) Bonds	232
9.4.3	E=E(p–p) Bonds	235
9.4.3	EE((p–p)) Bonds	237
10	Organoelement Compounds of Selenium and Tellurium (Group 16)	239
11	Organometallic Compounds of Copper, Silver, and Gold (Group 11)	249
11.1	Copper and Silver Organyls	249
11.2	Gold Organyls	262
	Organometallic Compounds of the Transition Metals
12	Introduction	275
12.1	The 18 Valence Electron (18 VE) Rule	276
	Excursion 7: Can the VSEPR concept be applied to transition-metal complexes?	282
12.2	Organometallic Catalysis: Some Fundamental Principles	284
13	-Donor Ligands	291
13.1	Preparation of Transition-Metal–Alkyl and –Aryl Compounds	292
13.2	Selected Properties of Transition-Metal -Organyls	295
13.2.1	Thermodynamic Stability versus Kinetic Lability	295
13.2.2	Interactions of C–H Bonds with Transition Metals	299
13.2.3	Interaction of C–C Bonds with Transition Metals	308
13.2.4	Transition-Metal Perfluorocarbon Complexes	312
13.3	Transition-Metal Organyls In Vivo	315
14	-Donor/-Acceptor Ligands	329
14.1	Transition-Metal–Alkenyl, –Aryl, and –Alkynyl Complexes	329
14.2	Transition-Metal Carbene Complexes	333
14.3	Transition-Metal–Carbyne Complexes	350
14.4	Metal Carbonyls	356
14.4.1	Preparation, Structure, and Properties	357
14.4.2	Variants of CO Bridging	360
14.4.3	Bonding Properties and Experimental Evidence	363
14.4.4	Principal Reaction Types	372
14.4.5	Carbonyl Metalates and Carbonyl Metal Hydrides	375
14.4.6	Carbonyl Metal Halides	378
14.5	Thio-, Seleno-, and Tellurocarbonyl Metal Complexes	379
14.6	Isocyanide Complexes (Metal Isonitriles)	381
	Excursion 8: Photochemistry of Organometallic Compounds	383
15	, -Donor/-Acceptor Ligands	395
15.1	Olefin Complexes	395
15.1.1	Homoalkene Complexes	395
15.1.2	Heteroalkene Complexes	413
15.1.3	Homo- and Heteroallene Complexes	415
15.2	Alkyne Complexes	424
15.2.1	Homoalkyne Complexes	425
15.2.2	Heteroalkyne Complexes	435
15.3	Allyl and Enyl Complexes	436
15.3.1	Allyl Complexes	436
15.3.2	Dienyl and Trienyl Complexes	445
	Excursion 9: NMR Spectroscopy of Organometallic Compounds	451
15.4	Complexes of the Cyclic -Perimeters C_nH_n	478
15.4.1	C₃R₃⁺ as a Ligand	479
15.4.2	C₄H₄ as a Ligand	480
15.4.3	C₅H₅^– as a Ligand	484
15.4.3.1	Binary Cyclopentadienyl–Metal Complexes	486
15.4.3.2	Cyclopentadienyl Metal Carbonyls	507
15.4.3.3	Cyclopentadienyl Metal Nitrosyls	511
15.4.3.4	Cyclopentadienyl Metal Hydrides	512
15.4.3.5	Cyclopentadienyl Metal Halides and Their Products	514
15.4.3.6	Special Applications of Metallocene Derivatives	518
15.4.4	C₆H₆ as a Ligand	528
15.4.4.1	Bis(arene)metal Complexes	528
15.4.4.2	Arene Metal Carbonyls	539
15.4.4.3	Other Complexes of the Type (₆-Arene)ML_n	543
15.4.4.4	Benzene Cyclopentadienyl Complexes	544
	Excursion 10: Organometallic Chemistry of Fullerenes	546
15.4.5	C₇H₇ as a Ligand	549
15.4.6	C₈H₈ as a Ligand	555
15.5	Metal–-Complexes of Heterocycles	560
15.5.1	S, Se, and Te Heterocycles	561
15.5.2	N Heterocycles	561
15.5.3	P and As Heterocycles	564
15.5.4	B Heterocycles	570
15.5.5	Metallaheterocycles	576
16	Metal–Metal Bonds and Transition-Metal-Atom Clusters	579
16.1	Formation of and Criteria for Metal–Metal Bonds	579
16.2	Dinuclear Clusters	584
16.3	Trinuclear Clusters	587
16.4	Tetranuclear Clusters	588
	Excursion 11: Structure and Bonding in Clusters – The Isolobal Analogy	590
16.5	Approaches to Systematic Cluster Synthesis	595
16.6	Pentanuclear and Higher Clusters	599
17	Organometallic Chemistry of the Lanthanoids and Actinoids	609
17.1	Comparative Considerations	610
17.2	Tour of the Ligands	614
18	Organometallic Catalysis in Synthesis and Production	635
18.1	Olefin Isomerization	635
18.2	C–C Coupling Reactions	637
18.2.1	Allylic Alkylation	638
	Excursion 12: Asymmetric Allylic Alkylation	640
18.2.2	The Heck Reaction	642
18.2.3	The Suzuki Reaction	645
18.2.4	The Stille Reaction	649
18.2.5	The Sonogashira Reaction	651
18.2.6	Hydrocyanation	652
18.3	C–Heteroatom Coupling	654
18.3.1	Amination of Arenes	654
18.3.2	Hydroamination	657
18.3.3	Hydroboration	658
18.3.4	Hydrosilation	659
18.4	Olefin Oxidation	660
18.5	Water-Gas-Shift and Fischer–Tropsch Reactions	665
18.6	Carbonylation of Alcohols	669
18.7	Hydrogenation of Alkenes	670
18.8	Hydroformylation	676
18.9	Reppe Syntheses	679
18.10	Alkene and Alkyne Metathesis	682
18.10.1	Alkene Metathesis	682
18.10.2	Alkyne Metathesis	688
18.10.3	Alkene–Alkyne Metathesis	689
18.11	Oligomerization and Polymerization of Alkenes and Alkynes	691
18.11.1	Oligomerizations	692
18.11.2	Olefin Polymerization	695
18.11.2.1	Polyethylene	697
18.11.2.2	Polypropylene	699
18.11.2.3	Homo- and Copolymerization; Functionalized Olefins, Cycloolefins, and Diolefins	706
18.11.2.4	Non-Group 4 Catalysts	709
18.11.2.4.1	Lanthanoidocene Catalysts	709
18.11.2.4.2	The Iron Age of Olefin Polymerization	710
	Appendix	717
A-1	Redox Reagents in Organometallic Chemistry	717
A-2	Nomenclature of Organometallic Compounds	721
A-3	Abbreviations and Symbols	726
A-4	Literature	732
	Author Index	761
	Subject Index	783

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