Reactivity of a Phosphido-Niobocene Derivative toward CS
2
and
Alkyl Halides to Give Phosphinodithioformato- and
Phosphino-Niobocene Complexes: X-ray Crystal Structures of
[Nb(η
5
-C
5
H
4
SiMe
3
)
2
(K
1
-S-SC(S)(PPh
2
))(CO)] and
[Nb(η
5
-C
5
H
4
SiMe
3
)
2
(P(I)Ph
2
)(CO)]I
3
Antonio Antin ˜olo,* Santiago Garcı ´a-Yuste, Antonio Otero,* Juan C. Pe ´rez-Flores,
Rebeca Reguillo-Carmona, Ana M. Rodrı ´guez, and Elena Villasen ˜or
Departamento de Quı ´mica Inorga ´ nica, Orga ´ nica y Bioquı ´mica, Facultad de Quimica, UniVersidad de
Castilla-La Mancha, 13071 Ciudad Real, Spain
ReceiVed NoVember 24, 2005
The reaction of the niobocene complex [Nb(η
5
-C
5
H
4
SiMe
3
)
2
(PHPh
2
)(CO)]Cl (1) with NaOH yielded
the corresponding phosphidoniobocene derivative [Nb(η
5
-C
5
H
4
SiMe
3
)
2
(PPh
2
)(CO)] (2) by deprotonation
of the P-H bond. The subsequent insertion reaction of carbon disulfide into the Nb-P bond yielded the
first examples of a diphenylphosphinodithioformato ligand coordinated to the niobocene system by giving
[Nb(η
5
-C
5
H
4
SiMe
3
)
2
(κ
1
-S-SC(S)(PPh
2
))(CO)] (3) and [Nb(η
5
-C
5
H
4
SiMe
3
)
2
(κ
2
-S,S-SC(S)(PPh
2
))] (4); the
latter compound can also be prepared by the corresponding CO elimination of 3. The cationic d
2
species
[Nb(η
5
-C
5
H
4
SiMe
3
)
2
(PRPh
2
)(CO)]X (R ) Me, X ) I(5); CH
2
Ph, X ) Br (6); CH
2
CH
2
Ph, X ) Br (7))
were prepared by the reaction of alkyl halides RX (R ) Me, X ) I; CH
2
Ph, X ) Br; CH
2
CH
2
Ph, X )
Br) with 2 by electrophilic attack on the phosphorus atom present in the phosphido terminal ligand. In
the same way, the reaction of 2 with ICH
2
CH
2
I yielded the complex [Nb(η
5
-C
5
H
4
SiMe
3
)
2
(P(I)Ph
2
)(CO)]-
I
3
(8). The molecular structures of 3 and 8 were determined by single-crystal X-ray diffraction studies.
Introduction
Dithiocarbamato ligands, R
2
NCS
2
-
, have attracted consider-
able attention in coordination chemistry,
1
mainly due to their
ability to form stable chelate complexes. However, very little
effort has been directed toward investigating the analogous
dialkylphosphinodithioformato ligands, R
2
PCS
2
-
. Indeed, only
a few well-characterized R
2
PCS
2
-
-containing complexes of
early-middle transition metals such as Zr,
2
Mo,
3
and W
4,5
have
been reported to date, and in these complexes, the ligand
coordinates to metal centers through the two S atoms
2
(a), the
P and S atoms by chelation
5a
(b), and either simple S- or
P-coordination
5b
(c and d) (see Figure 1).
A few years ago, we reported the synthesis of a new family
of complexes including [Nb(η
5
-C
5
H
4
SiMe
3
)
2
(PHPh
2
)L]Cl (1),
where L ) CO, CNR,
6
and these were prepared by an insertion
reaction of ClPPh
2
into the Nb-H bond of [Nb(η
5
-C
5
H
4
SiMe
3
)
2
-
(H)L)]. Treatment of derivative 1 with aqueous NaOH yielded
the corresponding neutral phosphidoniobocene complex [Nb-
(η
5
-C
5
H
4
SiMe
3
)
2
(PPh
2
)(CO)] (2) by deprotonation of the P-H
bond.
7
This complex represents an interesting starting material
to extend the phosphorus-containing niobocene chemistry. The
phosphorus atom from the phosphido terminal ligand has a lone
electron pair that is expected to give rise to interesting chemistry
that can be explored. We focused our attention on the synthesis
of new phosphorus-containing niobocene complexes from 2 by
exploring the possibilities for both the insertion reaction into
the Nb-P bond, using carbon disulfide as the reagent, and the
electrophilic attack on the P atom of the phosphido terminal
ligand in alkylation processes with several RX reagents. The
first type of reactivity has allowed the preparation of the new
niobocene containing the anionic diphenylphosphinodithiofor-
mato ligand, Ph
2
PCS
2
-
, namely, [Nb(η
5
-C
5
H
4
SiMe
3
)
2
(κ
1
-S-SC-
(S)(PPh
2
))(CO)] (3) and [Nb(η
5
-C
5
H
4
SiMe
3
)
2
(κ
2
-S-SC(S)-
(PPh
2
))] (4), and the second one, the isolation of a new family
of cationic d
2
18-electron complexes [Nb(η
5
-C
5
H
4
SiMe
3
)
2
-
(PRPh
2
)(CO)]X (R ) Me, X ) I(5); CH
2
Ph, X ) Br (6); CH
2
-
CH
2
Ph, X ) Br (7)). Finally, the reaction of 2 in the presence
of ICH
2
CH
2
I gave [Nb(η
5
-C
5
H
4
SiMe
3
)
2
(P(I)Ph
2
)(CO)]I
3
(8).
* To whom correspondence should be addressed. E-mail:
antonio.antinolo@uclm.es; antonio.otero@uclm.es. Fax: +34926295318.
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1310 Organometallics 2006, 25, 1310-1316
10.1021/om051013u CCC: $33.50 © 2006 American Chemical Society
Publication on Web 02/02/2006