_P.-Powell-auth.-Principles-of-Organometallic-Chemistry-Springer-Netherlands-1988

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The first three periodic groupsH HEt -Ct-~oR BuLi/ E '--OR, t-e-- + Bu Sn' THF, -78° "- 4SnBu3 U( e) DILITHIO DERIV ATIVES. 1, 1-Dilithiomethane has been obtained by pyrolysisof pure, salt free methyllithium (p. 3 5). The direct reaction between lithiummetal and dibromomethane gives only about 6% yield. A two step synthesisthrough a dimercury derivative is more successful.CH,l,Hg~ CH,(Hgi),--cCH,Li,4Li4Bu'Li+ 2Hg + 2LilCH,Li, + Bu~Hg + 2LiiThe preparation of 1, 1-dilithioethane illustrates several general organometallicreactions, including hydroboration and the transfer of organic groups fromone element to another. Dilithioethane is rather susceptible to decomposition intovinyllithium and lithium hydride through /3-hydrogen transfer.H2C=CH8r Mg/THF H C=CHM Br (i)B(OMe)3 H C=CHB(OBu") (i)H3B.THF2 g (ii)Bu"OH 2 2 (ii}Bu"OH3.3.2 Reactions of organolithium compounds and comparison withGrignard reagents(a) GENERAL REACTIVITY. Some reactions of organolithium compoundswhich illustrate their great versatility in synthesis are summarized in Fig. 3.8.The reactions ofthe corresponding and less reactive Grignard reagents (p. 50) areoften similar. Grignard reagents, for instance, do not metallate alkenes or arenes,although they do exchange with alkynes. Nucleophilic attack by Grignard andorganolithium reagents on multiple bonds such as ) C=O or -C=N leads afterhydrolysis to a wide range of organic products. It is generally most convenient touse the Grignard reagents to effect these classical transformations, as less rigorousprecautions are required. In a few instances, however, organolithium reagentsbehave differently. Carboxylate salts, for example, react as follows:44stoble to ottockby R'Li
'OXIDATION'ROHrOF STYRENES ANODIENESCOUPLINGFig. 3.8 Some reactions of organolithium reagents.6 6 6(A).o- o o y 6'1,2-oddition._____.: 1 ~ 1 Kinetic producienolote ion~&R(8).1,4-odditionThermodynomicproduciFig. 3.9 1. 2- and l, 4-addition of an organometallic compound to an ct/i-unsaturatedketone.
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Principles ofOrganometallicChemistr
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© 1988 P. PowellOriginally publish
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Contentsvi3.5 Beryllium 543.6 Calci
Page 8 and 9: Contents12.4 Chemistry based on syn
Page 10 and 11: PrefaceIn the 20 years since 'Princ
Page 12 and 13: Periodic table ofthe elementsThe pe
Page 14 and 15: Periodic table of elementsGroup Gro
Page 16 and 17: General surveysyntheses. They are a
Page 18 and 19: General surveypacked hexagonal, nic
Page 20 and 21: Table 1.1. Mean metal-carbon bond d
Page 22 and 23: General survey(c) COMPLEXES OF UNSA
Page 24 and 25: General survey4008.0o1E...,300.=; 2
Page 26 and 27: General surveyelements are rapidly
Page 28 and 29: General surveyCollman, J.P., Hegedu
Page 30 and 31: 100o-100o Si110111Ql-200 . 1L. :1o
Page 32 and 33: The main group elementsFor R = alky
Page 34 and 35: The main group elementsweakly exoth
Page 36 and 37: The main group elementselement and
Page 38 and 39: The main group elements(a) HYDROSIL
Page 40 and 41: The main group elementsinsertion:-
Page 42 and 43: The rnain group elernentsElectrophi
Page 44 and 45: The first three periodic groupsTabl
Page 46 and 47: The first three periodic groupstran
Page 48 and 49: The first three periodic groups(o)(
Page 50 and 51: The first three periodic groups( b)
Page 54 and 55: The first three periodic groupsorga
Page 56 and 57: The first three periodic groupsMe M
Page 60 and 61: The first three periodic groupsThis
Page 62 and 63: The first three periodic groupsHere
Page 64 and 65: The first three periodic groupselec
Page 66 and 67: The first three periodic groupsEt~5
Page 68 and 69: The first three periodic groupscond
Page 70 and 71: The first three periodic groupsThe
Page 72 and 73: 1 2·65 1 9-...:..... _;.;;.-c 1·4
Page 74 and 75: The first three periodic groupsCycl
Page 76 and 77: The first three periodic groups3. 7
Page 78 and 79: The first three periodic groupsYe\
Page 80 and 81: The first three periodic groupsor o
Page 82 and 83: Table 3.6 Some hydroborating agents
Page 84 and 85: RCf:0~HH~RCHO2 2Hi~OH-"' 18-C-R/ 1o
Page 88 and 89: The first three periodic groups(c)
Page 90 and 91: The first three periodic groupsTHF.
Page 94 and 95: The first three periodic groupspuls
Page 96 and 97: The first three periodic groupsROH/
Page 98 and 99: The first three periodic groupsthe
Page 100 and 101: The first three periodic groupsThe
Page 102 and 103: The first three periodic groupsin p
Page 104 and 105: The first three periodic groupsSilv
Page 106 and 107: The first three periodic groupso-RR
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The first three periodic groups(a)(
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The first three periodic groups5. W
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4Organometallic compoundsof element
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The main Groups IV and Vachieved e.
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The main Groups IV and Ve.g. alipha
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The main Groups IV and VDimethyltin
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The main Groups IV and V4.3.3 React
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The main Groups IV and Villustrates
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The main Groups IV and Vof methylco
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The main Groups IV and VTable 4.1.
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The main Groups IV and Vanes) are s
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The main Groups IV and Vconcentrati
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The main Groups IV and VTable 4.2.
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The main Groups IV and V4.6.3 Caten
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The main Groups IV and VTreatment o
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The main Groups IV and V4.8 pTC-JJT
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The main Groups IV and VA convenien
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The main Groups IV and Vfu- +( + )[
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The main Groups IV and Vand Me 2 PF
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The main Groups IV and VAcidH 2 PO(
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The main Groups IV and Vin World Wa
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The main Groups IV and VHX(SblPh M
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The main Groups IV and VOn replacem
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The main Groups IV and Varsenic yli
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The main Groups IV and VPh 2 BiBiPh
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The main Groups IV and Vphosphorus
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The main Groups IV and VDimethyltin
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5Some transition metalchemistry rel
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M L--4----f/~1 11 1\ 11 11 1\ 11 11
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Transition metal chemistryeven nega
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co co co cooc~o o co c~co cooc~c~ o
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Transition metal chemistryeach othe
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Transition metal chemistryconsidere
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Transition metal chemistryTable 5.3
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Transition metal chemistryTable 5.5
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Table 5.7. Thermochemical data and
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Transition metal chemistryNickel is
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Transition metal chemistry(o)(OC ln
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Transition metal chemistryCarbonyl
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Transition metal chemistry2Cr(COJ6
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Transition metal chemistry18-electr
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Table 5.8. General reactions of tra
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Transition metal chemistry5. 3.1 Ad
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Transition metal chemistrynot detec
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Transition metal chemistryPd(PPhBu~
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Transition metal chemistryH2 -LL3Rh
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Transition metal chemistryPhosphine
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Transition metal chemistry(d) Comme
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Transition metal chemistryD: 1 Hn.m
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Organometallic compounds of the tra
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No3-electron1] 3 -allyl4-electron17
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Organotransition metal chemistrymel
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Organotransition metal chemistryii)
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Table 7.2. Mechanisms of decomposit
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Organotransition metal chemistry4Ti
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Organotransition metal chemistryM e
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Organotransition metal chemistryIn
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Organotransition metal chemistryThe
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Organotransition metal chemistry~ (
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Organotransition metal chemistryo o
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Organotransition metal chemistry( C
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Organotransition metal chemistryMe
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Organotransition metal chemistry/OM
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Organotransition metal chemistry7.3
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Organotransition metal chemistryexc
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Organotransition metal chemistrysev
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Organotransition metal chemistry)--
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Organotransition metal chemistryR R
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Organotransition metal chemistry-co
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Organotransition metal chemistry4.
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Organotransition metal chemistry(b)
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r~...I.J::...--Î-..L-.._.,:;.I""'
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Allyl and diene complexessignals ar
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Allyl and diene complexesdoublets.
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Allyl and diene complexes111.5°. A
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Allyl and diene complexesThe pallad
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Allyl and diene complexesFe(C0} 5-F
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Allyl and diene complexes~4,neutrat
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Allyl and diene complexesThis indic
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Allyl and diene complexesonly with
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Allyl and diene complexesderivative
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Allyl and diene complexesvolatile,l
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Allyl and diene complexesChemical R
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9Five electron ligands9.1 lntroduct
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Five electron ligandsTable 9.1 The
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Five electron ligandsthe ferriceniu
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Five electron ligandsFerrocene unde
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Five electron ligands---v~···Fe,
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Five electron ligandsDihalogenometh
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Five electron ligands(c) TITANOCENE
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Five electron ligandsa pair of non-
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Five electron ligands9. 3.1 Mononuc
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Five electron ligandsslowly oxidize
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~ o coo,... ...,C,, /....-:;.' //Fe
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Five electron ligandsn-system of ea
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Five electron ligandsFig. 9.15 Mole
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Five electron ligandsNucleophilic r
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Five electron ligands(a) Sketch the
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lCH2=CHC2H5Five electron ligands(i)
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Five electron ligands( 6 A 1 g) and
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Complexes of arenesFor chromium thi
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Complexes of arenesW(C 6 H 6 ) 2
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Complexes of arenesgas phase (5.01
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Complexes of arenes(Q)-RCr cr(C0)
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Complexes of arenes- BH 3~jCr(C0) 3
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Complexes of arenesif"••d•R"x
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wNfoi::>.~7trienyl Cr(C0) 3~·trien
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Complexes of arenesmethyl iodide. T
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Complexes of arenesin the whole mol
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Complexes of arenesproposed above,
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Complexes of arenesProblems1. Ferro
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Complexes of arenes(<) ~PlMe~MeMe~M
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Table 11.1. Electron counting in cl
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Cluster compounds455TrigonalOctahed
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Cluster compoundsFig. 11.4 Closo, a
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Cluster compoundsmixture of the mor
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Cluster compoundsIt is extremely st
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Cluster compounds2- 2-~ m1 11O GQ8-
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Cluster compounds(IJ 5 -C,B,H 6 )Mn
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wUlo2-Fe(C0) 5redu cine;~C 7 H~BF4-
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Cluster compoundsdensations' do not
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Cluster compoundsA 3 A 78 78 12A 3c
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Cluster compoundsstructures of the
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Mechanisms of industrial processesT
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Table 12.2.Process Feedstock Cataly
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Mechanisms of industrial processesF
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Mechanisms of industrial processes1
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chaingrowth(alkeneinsertion)CH 3 CH
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r!~~NiJy ~ ' ,. -;,,.,~,;, ..'Ni'+2
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ţ/Ph)o-cPd =:) )cH0-C'-....Ph 2~-8
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Mechanisms of industrial processesH
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H2 C=CH2H2C=CH2[Ti]-R + C2H4coordin
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o[~] o ~ [f!- ~7:Jlinear[w]=CH~poly
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Me3 CCH2Li3HCI/WCL 6 W(=CBut)(CH2 B
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Mechanisms of industrial processesW
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Mechanisms of industrial processesT
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••~'"'"'" 7 ~;~13 :H~ r--------
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Mechanisms of industrial processesc
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Mechanisms of industrial processesO
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Mechanisms of industrial processesc
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Mechanisms of industrial processesH
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a)oIIIc1c1o1H /H'-cH2 ,l!--1 --H'.
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Mechanisms of industrial processesB
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Mechanisms of industrial processes5
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Lanthanides and actinidesA few exam
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Lanthanides and actinidesCp~LuCH 3
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IndexOrganometallic compounds are i
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IndexCarbon monoxide contd.bonding
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IndexEthylene glycol. see Ethane-1.
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IndexMetallocenes contd.reactions,
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IndexSilicon contd.-silicon bonded
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_P.-Powell-auth.-Principles-of-Organometallic-Chemistry-Springer-Netherlands-1988

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