John E.

Ellis
IJnI~ersihl
. ..,of - Minnesota
I The Teaching of Organometallic
Mmneapolis. Minnesota 55455

- I Chemistry to Undergraduates

The chemistry of metal carbonyls and related com- Tabla 1. Representative Exampler of Electronically Equivalent
pounds containing d-block transition metals in low formal Main Group and Transition Metal Species
oxidation states is very diverse ( I ) . However, because of the Elec-
strong tendency for the metals in these compounds to from
Needed
achieve a closed shell configuration, i t is possible to make for
very convincing analogies between the chemistry of many ~ a iG
n roup Closed
of these species and that of corresponding non-metallic Atom and Shell
main group compounds in which therk is a similar tendency Transition confi-
Metal gura- Corrarponding Corresponding
for the constituent elements to achieve a closed shell con- Analogue fion Anionic Forms Neutral Forms
figuration. Thus, the 18-electron rule, when applied with
discretion (2),i s as important in predicting and rationak- I and Mn(CO1, 1 !-and Mn(CO1,- 12and [ M n C O l , I ,
ing the stoichiometries, structures, and reactivity patterns S a n d Or(CO1,
IriCO),
2 5'-and Or(CO1,'-
[Ir(CO
,,,) b
SF and ror(co],l,
P,and I,r(COl,l,
of transition metal compounds containing CO, PF3, and
other s-acceptor lig&ds (3) as is the octet rule for com-
pounds containing nonmetals. In order to compare transi-
tion metal and nonmetal groups which have the same elec-
tronic requirements i t is useful to introduce the concept of b p r e r d n t ~ yknown &ly in t h e f o r m of derlvatwer.
electronically equivalent groups (4, S).' The latter are de-
fined as those species which require the same number of
electrons to attain a closed shell configuration. Representa- phines, phosphites, olefins, and similar *-acceptor ligands
tive examples of these are given in Table 1. The close stoi- can lose such ligands readily to form coordinatively unsatu-
chiometric and structural similarities in the main group rated molecules which have different electronic require-
and transition metal analogs indicated in Table 1arise nat- ments than the original species. This and related reactions
urally from the equivalent electronic requirements of these are extremely i m p & n t in the ability of these substances.
species. Perhaps the most striking similarity shown is the especially metal carbonyls, to function as effective reagents
ability of tricarhonyliridium, a 15-electron species which in-organic synthesis ( 6 ) ;As a result of the lability of carbon
requires three electrons to achieve a closed shell configura- monoxide groups in these compounds, whenever two or
tion, to form a molecule containing a tetrahedral array of more metal carbonyl groups are hound to an atom or ion
Ir(COh
, .. units. In this manner each iridium atom thereby there is a strong tendency for a condensation process t o
attains a closed shell configuration just as phosphorus, a;- occur which effectively results from intramolecular dis-
senic. or antimonv do in forming PA,Asd, or Sbr, respective- placement of carhonyl groups. The formation of metal car-
ly. ~ h u sthe
, 1r(&)3 unit may be said to mimic a pnicogen honyl cluster compounds, which have no precedence in
atom in fulfilling its valency requirements. main group chemistry, is the net result of such an interac-
More significant from the standpoint of descriptive tion. For example, although PhSn(Co(CO)& analogous to
chemistry, however, is the fact that many of these stoichio- PhSnX3 (X = halide or pseudohalide group), is a well de-
metrically related main group and transition metal species fined molecule, attempts to prepare the unknown carbon
also have strikingly similar reactivity patterns. For exam- analog, PhC(Co(CO)a)s, result in the formation of a cluster
ple, the parallels in the chemistry of metal carhonyl dimers, species PhC(Co(C0)3)3. Effectively, in this reaction, the
such as [Mn(CO)sJz,which contain two 17-electron metal Co(C0)a group, of pseudohalogen character, by losing CO
units and halogens, and especially pseudohalogens, which has changed to a Co(C0)3 group, of pseudopnicogen char-
contain two 7-electron units, are sufficiently far-reaching acter. In the case of germanium both PhGe(Co(C0)d~
that i t is useful to classifv the former as transition metal (III), PhGe(Co(C0)s)s (I), and an intermediate PhGeCo-
pseudohalogens. Also, available evidence indicates that 16- s(CO)11 (11) are known and may he interconverted as fol-
and 15-electron metal containing arouDs.. ex.. - . Fe(C0h and lows (7)
Co(C0)3, respectively, may be classified as tran-
sition metal pseudochalconides and pseudopnicogenides.
The latter terms apparently have not been used previously
and are derived from chalcogen (chalk former) and pnico-
gen (suffocating) which are group names for the VIa and
Va family of elements, respectively.
The above relationships are very useful in rationalizing
manv known reactivity. patterns
. of electronically equiva-
lent main group and transition metal species; however, it is
important to recognize, at the outset, that there are two im-
nortant
r - - ~ -limitations
- ~ ~
~~~~~ ~~~ in this scheme. The first is that oreano-
~ ~
"
transition metal species containing carbon monoxide, phos-

'The general idea of electronically equivalent groups was first

introduced by J. Halpern ( 4 ) ; however, the first to use this term
was apparently L. F. Dahl(5).
2 / Journal of Chemical Education
 The second important limitation is that organotransition have reactivity patterns which are best described as those of pseu-
metal species, unlike their main group counterparts, do not dohalides (14).
exist as stable entities when the transition metal has more 2) "Oxidation" by halogens or halogenoids to form interhaloge-
electrons than i t requiresto attain a closed shell configura- noids.
tion (3). Cobaltocene and nickelocene are two notable ex- [C,H,Fe(COXL + Mn2(CO),, -+
ceptions to this rule. They are both highly reactive and
paramagnetic molecules which tend to formally lose their 2CJ3s(C0)2FeMn(CO)5 (15)
"excess" electrons in reactions. I n contrast, numerous sec-
ond and higher row main group nonmetals and a few met-
[MnfC0),I2 + (SCN),
[h(W),I, + I, ~m&o), -
+ ZNCSMn(CO), (16)
(17)
als often undergo valence shell expansions in reactions, e.g.

Pa, + CI, + PCI, I, (SCN),

+
main group analogs CIS Ix + 2IC1
+ 2ISCN -
3) Disproportionation by Lewis bases.
(13)
(13)

Thus, there are many main group compounds such as

- , (.C H-.~-I S O-.I .SO?.
SbFc-. -. and SCL which have n o coun-
-. IF?.
terpart in organotransition metal chemistry. This observa-
tion serves to emohasize the i m ~ o r t a n c eof the 18-electron
rule in rationalizkg the stoichiimetry and the reactions of
orrranotransition metal species (2, 3). Indeed, there Dres-
en<ly exist no examples or monon&lear diamagnetic organ-
otransition metal species in which the metal has more elec-
trons than are req&ed,to attain a closed shell configura-
tion.
Except for these two limitations, however important,
H+
mononuclear organometal units which lack one, two, and
three electrons in achieving a closed shell configuration
main group analogs Br, + HOH +

may profitably he considered as large and polarizable pseu-
dohalogens, pseudochalcogens, and pseudopnicogens, re-
spectively.
The experimental basis for these analogies will now be
shown by comparing the reactivity patterns of compounds
containing 17-, 16-, and 15-electron organometal units with
those of corresponding compounds containing electronical-
ly equivalent nonmetal units. In this manner i t is hoped
not only to achieve a reasonably coherent and teachable
approach to the chemistry of metal carbonyls and related
species, but also to possibly arouse new interest in the
chemistry of the nonmetals.
Seventeen-Electron Organometalllc Groups
Seventeen-Electron metal groups like their seven-elec-
tron main - erouo. counteroarts are normallv found as dimer-
ic species, are often volatile, unless they are ionic such as
C O ~ ( C N ) ~ &and
, have chemical reactivity patterns which
are strikingly similar to those of the higher halogens, par-
ticularlv Iz and main -group. ~seudohalogens.
. Some pseudo-
haloge& are known only in the form of neutral iadicals,
e.g., bis(trifluoromethyl)nitroxide, (CF&NO (8)or mo-
noanions, e.g., azide, N3-. and fulminate, CNO-. Similarly,
there exist a few isolable but highly reactive metal carbonyl
free radicals, e.g., V(C0)e and ICr(C0)5 as well as other
species which are only known in the anionic form, e.g.,
N b ( c 0 ) ~ -and Ta(CO)6- (I). The principal characteristic
reactions of the metal carbonyls which are also characteris-
tic of main group pseudohalogens and halogens are as fol-
lows. Each is illustrated with representative examples.
1) Reduction by electropositive metals and other reducing
agents to metallic salts and other metal carhonyl derivatives; i.e.,
like halogens, these metal dimers can behave as oxidizing agents.
HrO
{[H,OBr]Brl =+ HOBr H,O+ + + Br- (21)
CI, +Me,N + [Me,NCI]CI (22)
The Lewis base induced disproportionation of carbonyl dimers
emphasizes the close similarity in the chemistry of these species
and halogens. Although Lewis base attack of neutral carhonyl di-
mers can also result in substitution reactions, with hard bases such
as those containing oxygen or nitrogen donor functions, dispropor-
tionation is favored over substitution. eaceot with ReK!Oim. .-
'There appear to be nb reports of 1.ewis base mdueed dispropor-
tionnrion of the latter substance, presumably because of the dXfifi-
culty oicleaving the Re-Re bond.
The disproportionation of halogens in neutral or basic aqueous
solution to give hypohalous acid (or hypohalites) and halide ion is
often cited as an important criterion for a substance to he consid-
ered a pseudohalogen (23). If the initial attack of water (or hy-
droxide ion) on hromine is analogous to that of trimethylamine on
bromine, it can be represented by the following scheme
Such an initial step seems reasonable in that the existence of
HzOBrf, B hmm~xoniumion, has been confirmed in acidified
+-
aqueous solutions of HOBr (21). Water does attack C O ~ C O ) ~ ,
beit slowly, because the earbonyl is practically insoluble in this
medium, but only salts of the type [Co(HnO).][Co(CO)dz have
been isolated (24). However, the presumed initial intermediate in
this reaction is CO(CO)IOH~+or CO(CO)IOH (20). The latter
species can he compared with HOI, also an extremely unstable
substance which readily disproportionates to iodide and iodate
(13). The detection of thermally unstable salts of the type [Co(CO-
)bROH][Co(CO)dgenerated from the interaction of alcohols (20)
with C d C 0 ) 8 provides additional support that water as well as
other hard Lewis bases interact with Coz(CO)a to initially form
salts of the type [Co(CO)~B][Co(CO)~] (18). Although other neu-
tral csrbonyl dimers are less reactive than C O ~ ( C Oexcept
) ~ , far

C O ~ ( C O+) ~2K -
2KCo(CO), (9)
-.
RedCOh the" are also thoueht
to give similar salts.
4) Hydrogenation
" to interact with hard Lewis bases

[C:J15FdCO)J9 + 2Mg + 1,2-C,H,Br2

Zn + Mn,(CO),,
+

-
2BrMgFe(CO),C,H, + C,H,
Zn(Mn(CO),),
(10)
(11)
Co,(CO),

[C&,Cr(COhL
+ H,
+ Ha
-
UOCC, CO, H,

3 150 atm
2HCo(CO),

ZHCr(W)3CeHs
(25)

(26)
XC,H,So + [CjHjCr(W)J2 +

+ H,
main group analog 2(C-,H,),Co + I* -
2[iCSH,),Co+][C,H,Cr(C0).,-]

2[fCjH,),Cot1I-
(12)

(13)
I, + 2HI

Metal carbonyl hydrides may either be prepared by hydrogenation

(13)

Just as neutral carhonyl dimers may be considered to be transition
metal pseudohalogens, the corresponding carhonyl monoanions
. hv.
of carhonvl dimers as shown above or. in most cases. more easilv
protonation of a eorrespondml: rsrhonyl monoanion The pruper-
ties of HCO~CO,~ are remarkably similar to those of HI, which is in
accord with the suggested pseuduhslogen character of the C O ~ C O ) ~

Volum 53.Number 1, January 1976 1 3

Table 2. A Comparison of Selected Properties of HCdCOI. and HI Fe(C0)a analoes in Table 3 resemble each other is astoh-
ishing.'For example, the dissociation constants of H2S (KI
= 5.7 X K7 = 1.2 X 10-Is) (39) are close to those re-
Thermal decomposition H, + Co CO],. r l o w l y H, + I,, r l o w l y ) ~ = 3.6 X
ported for H ~ F ~ ( c o (K1 and Kp = 1 X
at -2&(C (271 at 1 0 0 ' ~(281 10-14) (40). Both acids are also volatile, malodorous sub-
Percent dissociation of -100% (291 %loo%(231 stances. The treatment of S2- and F e ( C 0 ) i - with mercu-
H X in dilute aqueous
.. .
.... ...
<"l,lti""<
ry(I1) salts also gives the strikingly similar insoluble and
Rxn w i t h aqueous AgCo(CO1, put (301 A91 ~ p (231
t polymeric species HgS and HgFe(C0)r. The dark yellow
AgNO, iron compound is thought to have a structure containing
~ x wni t h 0 , H,O + co,(co], (311 H 9 0 + 1% (23) zig-zag chains, not unlike those found in red HgS (cinna-
Rxn w i t h CH,MgBr C H 4 + MgBrCo(COI4 CH, + M4Brl
1321 (231
bar). A black Pb(II) derivative, [PbFe(COh],, is also
known (41) and is formally analogous t o PbS.
There are many Fe(C0)4 analogs of sulfur compounds
which are stoichiometricallv reasonable and oresentlv un-
group. Some of these similarities are depicted in Tahle 2. A few known. Particularly intriguing examples, of potential im-
other neutral carhonyl hydride species are also strong acids; e.g., nortance in hioinoreanic chemistrv.
HV(CO)G(free acid is unknown) (33) and HCo(CO)(PF3)3(34); " " . include Fe(COL ana-
most others, e.g., H C O ( C O ) ~ P PHMn(CO)s,
~~, and HFe(C- logs of sulfur containing amino acids. Also, although
O)&Ha, are only slightly dissociated in water andlor alcohols Fe(C0)a analogs of CS2 and RaS+ are unknown presently,
(35), as are many of the hydroacids of main group pseudohalides they are of reasonahle stoichiometry. However, in these
(23). cases, the prohahle inherent instability of C=Fe double
5) Addition to Multiple Bonds honds and seven-coordinate carbonyl cations in the case of
C(Fe(CO)& and R3Fe(C0ht, respectively, may preclude
isolation andlor characterization of these and related
species. The important point, however, is that the factors
that contribute to the stability of organometallic com-
pounds are not fully understood. Indeed, such unknowns
I t is apparent from the above examples that metal car- make synthetic work in organometallic chemistry a partic-
bonyl dimers may profitably he considered as transition ularly exciting field full of unexpected results! The 18-elec-
metal pseudohalogens, so long as those reactions in which tron rule places definite limits on what Fe(C0)a analogs are
carbon monoxide is lost are excepted. Normally the latter possihle, however. For example, iron analogs of (CH3)zSOz
occur in the reactions of carhonvl dimers with soft Lewis or SCla are not expected to he stable species because, un-
bases such as phosphines and organic species containing like sulfur, the Fe(C0)r group cannot undergo valence shell
multiole honds. The above reaction of C o. d C 0 ) ~with C2Fd
- ~
expansion.
is, in fact, the only reported example of a neutral carbonyl Although the relationship between the reactivity pat-
dimer adding to an unsaturated organic species. An analo- terns of these Fe(C0)r derivatives and their electronically
gous reaction has been reported for Coz(CN)m6- with acet- equivalent main group counterparts has not heen explored
ylene (37) and tetrafluoroethylene (38). extensivelv or svstematicallv. there are a numher of reac-
tions of sulfur compounds and their Fe(C0)4 analogs which
Sixteen-Electron Organometalllc Groups suezest that the relations hi^ is a meaningful one, provided
Although less is known about the chemistry of species on& reactions are considered in which lois of carbon mon-
containing sixteen-electron groups such as Cr(C0)s and oxide from the Fe(CO)4 group or valence shell expansion of
Fe(CO)4, especially in their dianionic forms, than that of the sulfur does not occur. In this context the Fe(CO)4
species containing seventeen-electron groups, the available group may profitably he considered a large polarizable
information is largely consistent with a description of these pseudochalcogen and thus Fe(C0)b and Fe(C0)4 should
snecies as oseudochalconides. For examole. . . there exist a have reactivity patterns analogous to those of carbonylsul-
numher of sulfur compounds in which the sulfur atom may fide and atomic sulfur. Figures 1 and 2 show that for a
he formallv - reolaced
. hv an Fe(CO)a . erouD. without drasti- numher of reactions such analogies are valid. The unstable
cally altering the structure or in certain cases the reactivity intermediates arising from the reaction of OH- with SCO
patterns of the species. A numher of examples of sulfur and Fe(C0)s in Figure 1 are assumed to be protonated on
compounds and their Fe(C0)r analogs are shown in Tahle
3.
The ability of the Fe(C0)4 group to mimic the behavior
of a sulfur atom arises because they are electronically
equivalent species in the sense that both Fe(C0L and S are
two electrons short of attaining a closed shell configuration.
On this basis these species may be anticipated to display
carbenoid behavior. The degree to which certain sulfur and

Table 3. Sulfur C o m ~ o u n dand

r FdCOI. Analogr

5, atomic
IUlfU,
sz-
HS-
.--..
HFe(CO1 -
Hz?_ H,F~(CO!, % _
52 ~Fe(COl.I._
NCS- NCFe(CO1,
HgS HgFe(CO1,
OCS OCFe(CO1,
Ph PS Ph uFe(CO1
cH?,NcS CH~,NCF~(C~],
(CHsO]C6H&S ~CH301C6H5CFe~COl,
(a thione ester) (a "carbene" complex]

U a n intermediate generated by thermal or photoiytic decomuori- Figure 1. Comparison of the reactivity patterns of COS and Fe(C0). (refer-
tion of Fe(CO1,. ences in parentheses).

4 1 Journal of Chemical Education

 The high yields of vinyl ethers obtained from this reaction
(82% in the above example) suggest that the method may
he a synthetically useful route to these species. A hetaine-
like intermediate (IV) was proposed to form via an initial
nucleophilic attack of the Wittig reagent with the carhene
[Fe(COl,h L Fe(CO):b' % (oc)&+ complex
and 1or CHI
of Fe(CO),
147) PhlPFe(CO),

Fioure 2. Cmmarison
-~ 7~ ~~
. .. chemistrv. (references
of sulfur and FalCOI. . in oaren-
An entirely analogous intermediate (V) has been suggested
theses) a, Reactions of base with Sg: atomic sultur would undoubtedly yield
the same product. b, Generated by heating w photolyring Fe(C0)s. to form in the reaction of PhaPCHz with ethvlhenzoate
(61). However, in this case, the intermediate

the sulfur and iron, respectively. Also, although ethylene

sulfide in Figure 2 is normally formulated as a a-complex,
it has also been reoresented as a s-comolex (42) similar to
T-CZH~F~(CO)~.
Many profitable comparisons between sulfur and
M(C0)5 (M = Cr, Mo, W) chemistry may also he made, al-
though the M(CO)s unit appears to be extremely reluctant
to form species of the type RzM(C0)5, where M is seven-
coordinate. Perhaps the most striking similarities in the S
and M(C0)5 groups are found in a comparison of the chem-
istries of organic esters and M(C0)5 stabilized carbenes.
".
Comnlexes of the tvoe M(C0R)R' where M = M(CO)s have
beenAdescribedby the following resonance forms
OR OR
\
R'
Fischer and coworkers have noted significant parallels in
eliminates an etboxide ion giving the salt (PbaPCHzCO-
Ph)OEt. Subsequently, the anion abstracts an a hydrogen
forming ethanol and PhsPCHCOPh instead of the vinyl
ether. Undoubtedly, the W(CO)s unit is not as effective as
oxygen in causing such elimination reactions. Sulfur should
also be less effective than oxygen in this regard; however,
the interaction of Wittig reagents with the less accessible
thioue esters has apparently not been investigated.
Fnteen-Electron Organornetalllc Groups
Transition metal groups such as Co(C0)3, Mn(CO)d,
V(C0)5, s-CsHsFe(CO), s-C5H5Cr(C0)2, etc. are 15-elec-
tron species and electronically equivalent to group Va
atoms which comprise the pnicogen family of elements.
The best known 15-electron s ~ e c i e sis tricarbonvlcobalt
~ ~

the structures and reactivity patterns of metal carbenes which may be isolated as a tetraker, [Co(CO)& he latter
- .
and oreanic esters. For examole.. the X-rav crvstal struc-
ture of pentacarbonylphenylmethoxycarbenetungsten
- contains a tetrahedral arrav of cobalt atoms (VI). Similarlv,
tricarbonylrhodium and tricarbonyliridium are isolated as
shows that the carbene moietv in this snecies closelv resem- tetramers, [M(CO)& (M = Rh, Ir). The cobalt and rho-
bles that of methyl henzoate (59). he ability bf these dium species (VI) contain three bridging carhonyl groups
metal carbenes to undergo aminolysis, base addition, and while Ir3(C0)12 possesses only terminal carbonyls, having a
base exchange reactions is also in accord with their ester- structure strictly analogous to that of the molecular forms
like behavior. Resonance forms similar to the preceding of P , As, and Sh.
have been invoked to account for the chemical properties of
oraanic esters, i.e.

X=O,S
Since M(CO)s units are electronically equivalent to an oxy-
gen or sulfur atom, such a correspondence should not he
surprising. Particularly interesting work on metal carbeues
which exploits their dipolar character has recently been re-
ported by Casey and coworkers. For example, methylene- The ability of the Co(C0)s group to formally replace one
triphenylphosphorane reacts with the ester-like carbene or more arsenic or phosphorus atoms in As4 or Pq, while
complex, pentacarbonylphenylmethoxycarhenetungsten preserving the basic tetrahedral structure of the molecule,
according to the following equation provides the most dramatic demonstration of its pseudo-
pnicogen character. Such a formal replacement scheme is
,CA shown below. Only compound (XI) is presently unknown;
( O c ),wc + Ph,PCH> + however a phosphorus sulfide analog, Co3iCO)gPS has been
'OCH, prepared recently (63).
Volume 53. Number 1, January 1976 1 5

(XI) cxn) (13)
Monomeric species containing an M(C0)z unit such as
H3M(C0)3 (M = CO, Rh, Ir) would also have the preferred
closed shell configuration like their main group analogs,
N H 3 , PHs, A s H 3 , etc. Although the former species are un-
known, phosphine substituted derivatives including
H s M ( P R d 3 , R = alkyl or aryl, M = Co (64) and M = Ir
(65) and H 3 I r C O ( P P h 3 ) 2 (66) have been reported.
Fifteen-Electron groups could also satisfy their d e n c e
requirements by forming dimers containing M-M triple
honds instead of tetramers containine M-M sinele bonds.
The vast majority of these do indeeh form tetrimers in-
cluding M ( C 0 ) 3 (M = Co, Rh, Ir), CSHSM(CO)(M = Fe,
Ru), and HM(C0)z (M = Ru, 0s). However, there are two
unusual electronically equivalent groups C S M ~ ~ M ( C(M O)~
= Cr, Mo) which arepreiently uniquein their ability to at-
tain closed shell configurations by dimerizing and forming
formal M-M trinle bonds. The cwstal structure of the Cr
analog has been determined by X-ray diffraction and con-
firms the presence of a very short Cr-Cr bond (67). Other
15-electron groups also are known to form triple bonds, the
most celebrated of which are Fischer's carhyne complexes,
e.g., B r ( C O ) 4 M = C - C H 3 (M = Cr, Mo, W) (68). However,
for many years analogous nitride complexes such as
C12(PEtzPh)3Re=N (69) have been known, where N is
electronicallv- eauivalent
- with a neutral carbvne e r o u D .
Carhyne groups can also be stahilized by coordina$on &I
Co(CO)s eroups as shown in structure (XIII) (70).Effec-
tively, ( X ~ I Iarises) through a formal substitution of a car-
byne group for an electronically equivalent Co(C0)z group
in C o 4 ( C 0 ) ~ 2 ,though (XIII) unlike C o 4 ( C O ) ~ 2has no hridg-
ing carhonyl groups (cf. Structure (XII)). Similar phospho-
rus analogs, such as P 3 C C H 3 have not been reported, al-
though they should be capable of existence.
tCO1,
(xm)
Concluding Remarks
Many far-reaching parallels have been shown to exist in
the chemistry of organotransition metallic and non-metal-
lic compounds as long as only those reactions are consid-
ered in which loss of a ligand (e.g., carbon monoxide) from
the metal or valence shell expansion of the nonmetal does
not occur. The concept of electronically equivalent groups
allows one to correlate these parallels and to rationalize
many observed trends in organotransition metal chemistry.
The importance of using these analogies in predicting new
reactivity patterns of organotransition metallic compounds
is largely unknown. Their assessment and application may
represent a significant area of organometallic research in
the future.
8 / Journal of Chemical Education
Acknowledgment
I am grateful to the donors of the Petroleum Research
Fund (PRF 2670-G3) administered by the American
Chemical Society, and to the Graduate School of the Uni-
versity of Minnesota for support of this work.
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