Formation of (vinyl-ferrocenyl)stibines involving β-elimination: Hypervalent Sb-N bonding

Article abstract of DOI:10.1016/j.jorganchem.2007.04.020

Unusual syntheses of vinyl substituted ferrocenylstibines viz. diphenyl(2-vinylferrocenyl) stibine (2) and iodo-(N,N-dimethylaminoethylferrocenyl)(2-vinylferrocenyl)stibine (4) involving β-elimination, are reported. Stibines Ph₂SbFc (1) or Fc₂SbCl (3) containing dimethylaminoethyl-pendant arm on a ferrocenyl ring on reaction with MeI gives vinyl substituted ferrocenylstibines. All the new stibines were characterized by IR, mass, ¹H, ¹³C, COSY, HETCOR NMR spectroscopy. The structures of all of these 1,2-disubstituted ferrocenylstibines were determined by X-ray diffraction analyses. The compounds 3 and 4 show hypervalent bonding between the antimony and nitrogen atoms giving 6 and 5 coordinated antimony, respectively. This is the first report on ferrocenylstibines containing a vinyl group in their framework.

Full text of DOI:10.1016/j.jorganchem.2007.04.020

Journal of Organometallic Chemistry 692 (2007) 3486–3491
www.elsevier.com/locate/jorganchem
Formation of (vinyl-ferrocenyl)stibines involving b-elimination:
Hypervalent Sb–N bonding
a
a,
a
a
a
a
*
´
´
´
Jaime Vazquez , Pankaj Sharma , A. Cabrera , A. Toscano , S. Hernandez , J. Perez ,
b
´
R. Gutierrez
a
Departamento de Quı´mica Inorga´nica, Instituto de Quı´mica, UNAM, Circuito Exterior Coyoaca´n 04510, Me´xico D.F., Mexico
b
Facultad de Ciencias Quı´micas, Universidad Auto´noma de Puebla, Puebla, Mexico
Received 17 January 2007; received in revised form 17 April 2007; accepted 17 April 2007
Available online 22 April 2007
Abstract
Unusual syntheses of vinyl substituted ferrocenylstibines viz. diphenyl(2-vinylferrocenyl) stibine (2) and iodo-(N,N-dimethylamino-
ethylferrocenyl)(2-vinylferrocenyl)stibine (4) involving b-elimination, are reported. Stibines Ph2SbFc (1) or Fc2SbCl (3) containing dim-
ethylaminoethyl-pendant arm on a ferrocenyl ring on reaction with MeI gives vinyl substituted ferrocenylstibines. All the new stibines
were characterized by IR, mass, 1H, 13C, COSY, HETCOR NMR spectroscopy. The structures of all of these 1,2-disubstituted ferroce-
nylstibines were determined by X-ray diffraction analyses. The compounds 3 and 4 show hypervalent bonding between the antimony and
nitrogen atoms giving 6 and 5 coordinated antimony, respectively. This is the first report on ferrocenylstibines containing a vinyl group in
their framework.
ꢀ 2007 Elsevier B.V. All rights reserved.
Keywords: Ferrocenyl; Stibines; Hypervalent antimony
1. Introduction
ation, hidrosilylation [15–17], however, most of the reports
on these phosphines contain other donor atoms such as P,
O, and N apart from one phosphorus atom. Ferrocene
ligands that combine the usual donor groups with poten-
tially p-donating functionalities such as alkenyl groups still
present an area remaining largely a virgin field, which
markedly contrasts with the number of functionalized
vinylferrocenes already known. For instance, racemic
vinylferrocenes bearing an additional functional group
(Cl, C(O)Ph, C(OH)Ph2, C(O)NHPh) in position 2 of the
ferrocene unit were prepared by base-induced elimination
from the respective (2-ferrocenylethyl)ammonium salts
[18,19].
Recently, the chemistry of hypervalent compounds bear-
ing heavier pnictogens (in particular Sb, Bi) has attracted
interest [1–6]. Intramolecular interactions between anti-
mony and nitrogen atoms have been widely reported [7–
13], and 2-(Me2NCH2)C6H4-and 8-(Me2N)C10H6-moieties
have often been applied to stabilize organoantimony
molecular complexes, cations, or compounds containing
metal–metal bonds [9–13]. Our group has reported the first
ferrocenylstibines containing a 2-dimethylaminomethyl
and a 2-dimethylamino ethyl side chain. These stibines also
present Sb–N hypervalent interactions [14].
On the other hand, 1,2-disubstituted bidentate ferroce-
nylphosphines are important catalytic precursors for many
different types of reactions, e.g., hydrogenation, carbonyl-
Similarly, phosphorus substituted vinylferrocenes were
also synthesized either unintentionally or served just as
reaction intermediates [20]. Here, we wish to report the
unusual formation of (vinyl-ferrocenyl)stibines by a salt
formation reaction of dimethylaminoethylferrocenyl sti-
bines with MeI (Scheme 1).
*
Corresponding author. Fax: +52 555 6162217.
E-mail address: pankajsh@servidor.unam.mx (P. Sharma).
0022-328X/$ - see front matter ꢀ 2007 Elsevier B.V. All rights reserved.
doi:10.1016/j.jorganchem.2007.04.020

J. Va´zquez et al. / Journal of Organometallic Chemistry 692 (2007) 3486–3491
3487
Me
Me
(R,S)
(R,S)
NMe2
SbPh2
NMe2
SbPh2
tBuLi
Ph2SbCl
MeI
Fe
Fe
Fe
(RFc/SFc
)
(RFc/SFc
)
I
II
tBuLi
SbCl3
Me
Me
(R)
Me
(R)
Me
(S)
(S)
Me2N
NMe2 Me2N
NMe2
MeI
+
Sb
I
Sb
Cl
Sb
I
Fe
(RFc)
Fe
Fe
(RFc
)
(RFc
)
Fe
Fe
Fe
(SFc
(SFc
)
(SFc
)
)
S RFc SFc
R RFc SFc
III
IV
Scheme 1.
2. Results and discussion
All the compounds are soluble in CH2Cl2 and CHCl3.
These stibines are stable on melting without decomposition.
These compounds were analyzed by FAB+ mass spectrome-
try. For all the three compounds molecular ion peaks were
observed along with fragments corresponding to the succes-
sive loss oforganic entities attached tothe antimony atom. In
the far IR spectra of these compounds, Sb–C vibrations have
been observed. In all the compounds, the assignment of indi-
vidual proton signals in the 1H NMR spectra was based on
JHH coupling constant values and was confirmed by COSY
The ferrocenyl stibines (1) and (3) were synthesized by
treatment of Rac.(N,N-dimethylamino)ethylferrocene with
tBuLi, followed by electrophilic attack with Ph2SbCl or
SbCl3, respectively. It is to be noted that when (N,N-dim-
ethylamino)ethylferrocenyl stibines (1) and (3) react with,
one or more equivalent of MeI, the corresponding (vinyl-
ferrocenyl)stibine were obtained. A similar formation of
the corresponding phosphorus analogue of (2) was
reported [20]. It is worth mentioning that when the side
arm is Me2NCH2, a trimethylammonium salt was obtained
and its crystal structure was reported by our group.
Fig. 2. Molecular structure of chloro-bis(N,N-dimethylaminoethylferr-
ocenyl)stibine (3).
Fig. 1. Molecular structure of diphenyl (2-vinylferrocenyl)stibine (2).

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J. Va´zquez et al. / Journal of Organometallic Chemistry 692 (2007) 3486–3491
Fig. 3. Molecular structure of iodo-(N,N-dimethylaminoethylferrocenyl)(2-vinylferrocenyl)stibine (4).
and HETCOR. The molecular structures of 2, 3, and 4 have
been confirmed by X-ray crystallography as shown in Figs.
1–3. All these compounds are monomeric in nature and no
significant intermolecular interactions were observed. All
the three compounds possess planar chirality but com-
pounds 3 and 4 also possess central chirality. Compound 3
is enantiomerically pure and corresponds to the diastereoiso-
mer [R(C11),S(C25),S(Fc1),R(Fc2)] which was confirmed
by the Flack parameter, while compound 4 corresponds to
Sc,RFc (and Rc,SFc) diastereoisomers Scheme 1. Crystal
data for all structural analyses are given in Table 1. Selected
bond lengths and angles for all compounds are listed in Table 2.
The average Sb–C(ferrocenyl) bond length found in these
ferrocenylstibines is 2.123 A, which is slightly shorter than
˚
that found in the other known tertiary stibines. The short-
est Sb–C(ferrocenyl) bond length is ascribe to the effect of
bidentate and electron donating. This may be due to the
pp–dp bonding to a greater extent and thus shortening of
Sb–C bond ferrocenyl group in all the compounds.
The Sb–C(ferrocenyl) bond distance found in compound 2 is
˚
2.135(4) A, which is slightly larger than Sb–C(ferrocenyl) dis-
˚
tance found in previously reported stibine (1) [2.124(2) A],
which may be due to the extended conjugation and hence
decreasing the donor ability of ferrocenyl group. The Sb–C
Table 1
Crystallographic data for compounds 2–4
Compounds
2
3
4
Empirical formula
Formula weight
Crystal color and shape
Crystal system
C
487.01
Yellow prism
Triclinic
24H21FeSb
C28H36ClFe2N2Sb
669.49
C26H29Fe2INSb
715.85
Orange prism
Triclinic
Orange prism
Orthorhombic
P212121
0.326 · 0.162 · 0.072
12.4021(8)
13.1049(9)
17.055(1)
90
90
90
2771.9(3)
4
1.604
ꢀ
ꢀ
Space group
P1
P1
Crystal size (mm)
0.34 · 0.10 · 0.06
7.5690(7)
10.3697(10)
13.3918(13)
70.275(2)
84.266(2)
84.068(2)
981.75(16)
2
1.647
2.118
2.09–25.03
8052
3448
0.46 · 0.10 · 0.05
9.8530(7)
11.9888(8)
12.1523(8)
83.044(1)
72.712(1)
66.278(1)
1254.84(15)
2
1.895
3.453
1.76–25.00
10361
4424
˚
a (A)
˚
b (A)
˚
c (A)
a (ꢁ)
b (ꢁ)
c (ꢁ)
3
˚
V (A )
Z
Dcalc (g/cm3)
l (mmÀ1
2h (ꢁ)
)
2.116
1.96–25.01
22661
4886
0.0536
Reflections collected
Independent reflections
Rint
0.0426
0.0459
R1[I > 2r(I)]
0.0368
0.0383
0.0441
Flack’s parameter
Goodness-of-fit
Maximum/minimum Dq (e A
0.00(3)
1.007
0.8539/À0.6042
0.943
0.8810/À0.6350
0.949
0.8519/À0.4180
À3
˚
)

J. Va´zquez et al. / Journal of Organometallic Chemistry 692 (2007) 3486–3491
3489
Table 2
Selected bond length (Aꢁ) and selected bond angles (ꢁ) for compounds 2–4
Compound 2
Compound 3
Compound 4
Sb–C(1)
Sb–C(19)
Sb–C(13)
2.135(4)
2.157(4)
2.161(4)
Sb(1)–C(1)
Sb(1)–C(15)
Sb(1)–Cl(1)
Sb(1)–N(1)
Sb(1). . .N(2)
2.093(5)
2.144(5)
2.515(2)
2.584(5)
3.614(6)
Sb(1)–C(1)
Sb(1)–C(11)
Sb(1)–N(1)
Sb(1)–I
2.124(6)
2.131(6)
2.646(5)
2.8537(6)
C(1)–Sb–C(19)
C(1)–Sb–C(13)
C(19)–Sb–C(13)
96.36(15)
94.62(15)
97.09(15)
C(1)–Sb(1)–C(15)
C(1)–Sb(1)–Cl(1)
C(15)–Sb(1)–Cl(1)
C(1)–Sb(1)–N(1)
C(15)–Sb(1)–N(1)
Cl(1)–Sb(1)–N(1)
C(1)–Sb(1)–N(2)
C(15)–Sb(1)–N(2)
Cl(1)–Sb(1)–N(2)
N(1)–Sb(1)–N(2)
95.3(2)
C(1)–Sb(1)–C(11)
C(1)–Sb(1)–N(1)
C(11)–Sb(1)–N(1)
C(1)–Sb(1)–I
C(11)–Sb(1)–I
N(1)–Sb(1)–I
97.3(2)
71.4(2)
90.0(2)
90.52(16)
94.25(16)
161.85(12)
91.13(16)
98.85(15)
73.19(19)
88.54(18)
163.29(12)
142.74(17)
60.34(19)
118.57(11)
78.10(15)
(ferrocenyl) bond distance is shorter than the average Sb–C
(phenyl) bond lengths presented in the compound 2. In the
same manner the average Sb–C(ferrocenyl) bond distance
mined on a Perkin–Elmer 240. Melting points were
obtained on a MEL-TEMP II Fisher and are uncorrected.
EI and FAB+ mass spectra were recorded on a JEOL
SX102 double-focusing mass spectrometer with reverse
geometry using a 6-kV Xenon beam (10 am); nitrobenzyl
alcohol was used as matrix for recording the mass spectra.
IR spectra were recorded on a Nicolet-Magna 750 FT-IR
spectrometer as nujol mulls. 1H and 13C NMR spectra were
recorded in CDCl3 or CD3OD on JEOL ECLIPSE 300
(1H: 300.5311 MHz; 13C: 75.5757 ) spectrometer.
˚
found in compound 4 is 2.131(6) A is slightly longer than
the Sb–C(ferrocenyl) bond distance observed in stibine (3).
In compound 2, geometry around antimony is pyramidal
and the average C–Sb–C angle is 96.02(2), which is not very
different from the bond angles found in other tertiary sti-
bines [21–24]. The vinyl group is directed toward the diphe-
nylstibino substituent while remaining parallel with the
parent cyclopentadienyl ring, which allows an efficient con-
jugation that is demonstrated by the angles by C@C bond
and the Cp1 planes [À11.51(6)ꢁ]. The structure is very sim-
ilar to recently reported phosphorus analogues [25]. In com-
pound 3 and 4 distance between nitrogen atom of NMe2
3.1. X-ray crystallography
The X-ray intensity data were measured at 293 K on a
Bruker SMART APEX CCD-based X-ray diffractometer
by using monochromated Mo Ka radiation (k = 0.71073
˚
group and the central antimony atom is 2.584(5) A and
˚
˚
2.646(5) A, which is much shorter (69%) and (71%), respec-
A). The detector was placed at a distance of 4.837 cm from
˚
tively, than the sum of their Van der waals radii (3.74 A).
the crystals in all cases. Analysis of the data showed in all
cases negligible decays during data collections. An analyt-
ical face indexed absorption correction was applied. Crys-
tal structures were refined by full-matrix least squares.
SMART software (data collection and data reduction) and
SHELXTL were used for solution and refinement of the
structures.
These distances are slightly longer than the covalent bond
˚
length of 2.11 A [26]. This result indicates hypervalent bond
formation between antimony and nitrogen. There exists
another very weak hypervalent Sb–N interaction
˚
[3.614(6) A] in compound 3 which gives tetragonal bipyra-
mid geometry around the antimony atom in this compound
where two carbons and two nitrogen form the tetragonal
plane while lone pair and chlorine occupy the apical posi-
tions. In compound 4, the geometry about antimony atom
is distorted pseudo trigonal bipyramid where the two car-
bon atoms bound to the antimony atom (1Fc and 1Fc)
occupy the equatorial plane. The apical positions are occu-
pied by the nitrogen atom and the carbon atom of phenyl
group with a C–Sb–N angle 158.7ꢁ. The lone pair of elec-
trons can be considered to occupy the equatorial position.
3.2. Syntheses
3.2.1. Synthesis of diphenyl(N,N-dimethylaminoethyl-
ferrocenyl)stibine (1)
Compound 1 was synthesized according to our earlier
report [14].
3.2.2. Synthesis of diphenyl(2-vinylferrocenyl) stibine (2)
In a Schlenk tube, to a solution of stibine 1 (0.6 g,
1.1 mmol) in CHCl3 (20 ml), was added CH3I (3.2 mmol)
with continuous stirring. The reaction was stirred for 2 h
and the solution was concentrated under vacuum to obtain
an abundant yellow solid product, which was isolated by
filtration on a glass filter. The compound was dried and
3. Experimental
All the solvents were distilled immediately prior to use.
All the reactions were performed under an atmosphere of
oxygen-free dry nitrogen. Elemental analyses were deter-

3490
J. Va´zquez et al. / Journal of Organometallic Chemistry 692 (2007) 3486–3491
recrystallized from chloroform. Yield: 95%; m.p.: 115–
117 ꢁC; IR (m, cmÀ1): 472 (Sb–C), 1627 (C@C), 2960,
2923 (C–H stretch), 3063 (C–H aromatic). FAB+ m/z:
486 (100%) [M]+, 409 (49%) [MÀPh]+, 331 (16%)
[FcCH@CH2Sb]+, 212 (59%) [FcCH@CH2]+; 1H NMR
(CDCl3, d in ppm): 3.75 (m, 1H, CH, C5H3), 4.03 (s, 5H,
CH, C5H5), 4.34 (t, 1H, JHH = 2.4 Hz, CH, C5H3), 4.68
(m, 1H, CH, C5H3), 5.00 (dd, 1H, JHH = 1.3 Hz,
JHH = 1.1 Hz, CH@CH2), 5.29 (dd, 1H, JHH = 1.3 Hz,
JHH = 1.4 Hz, CH@CH2), 6.55 (2d, 1H, JHH = 10.7 Hz,
JHH = 10.7 Hz, CH@CH2), 7.26–7.57 (m, 10H, Ph); 13C
NMR (CDCl3, d in ppm): 68.3 (CH, C5H3), 69.8 (CH,
C5H5 ), 71.4 (CH, C5H3), 72.0 (CH, C5H3), 75.0 (C–Sb,
C5H3), 112.4 (C–CH@CH2), 128.3 (CH@CH2), 128.7
(CH@CH2 ), 133.7 (CH, Ph), 135.1 (CH, Ph ), 135.8
(CH, Ph ), 136.9 (C–Sb, Ph ).
1622 (C@C), 2991, 2875 (C–H stretch). FAB+ m/z: 716
(6%) [M]+, 588 (20%) [MÀI]+, 543 (20%) [MÀIÀNMe2]
1
333(12%) [FcCH@CH2Sb]+ 212 (25%) [FcCH@CH2]+; H
NMR (CDCl3, d in ppm): 1.04 (d, 3H, JHH = 6.7 Hz,
CH3), 1.76 (br s, 6H, Me2N), 4.09 (m, 1H, CH–H3C),
4.13 (m, 1H, CH, C5H3), 4.36 (s, 5H, C5H5), 4.19 (s, 5H,
C5H5), 4.26 (t, 1H, JHH = 2.1 Hz, JHH = 2.3 Hz, CH,
C5H3), 4.29 (s, 5H, CH, C5H5), 4.33 (m, 2H, CH, C5H3),
4.48 (m, 1H, CH, C5H3), 4.69 (m, 1H, CH, C5H3), 5.07
and 5.10 (dd, 1H, JHH = 1.1 Hz, JHH = 1.1 Hz, CH@CH2),
5.32 and 5.38 (dd, 1H, JHH = 1.1 Hz, JHH = 1.0 Hz,
CH@CH2), 6.68 (2d, 1H, JHH = 10.7 Hz, JHH = 10.6 Hz,
CH@CH2); 13C NMR (CDCl3, d in ppm): 7.5 (CH3–CH),
31.50 (NMe2), 61.2 (CH–CH3), 64.7 (CH, C5H3), 67.4
(CH, C5H3), 69.2(CH, C5H3), 69.4 (CH, C5H3), 70.1 (CH,
C5H3), 70.2 (CH, C5H5), 71.0(CH, C5H5), 71.3 (CH,
C5H3), 87.6(C–Sb, C5H3), 95.1 (C–Sb, C5H3), 111.2
(CH@CH2), 136.0 (CH@CH2).
3.2.3. Synthesis of chloro-bis(N,N-dimethylaminoethyl-
ferrocenyl)stibine (3)
To a solution of antimony trichloride (1.36 g, 6 mmol)
in ether (10 ml), a-(N,N-dimethylamino)ethylferrocenylli-
thium (2.55 g, 10 mmol) {synthesized in situ according to
reported method [14]}, was added drop-wise under a nitro-
gen atmosphere at –20 ꢁC with continuous stirring. The
mixture was further stirred for 24 h at room temperature
and then reaction was quenched with ice. After extraction
with dichloromethane (3 · 10 ml) and drying over sodium
sulfate, solvent was removed under vacuum. The com-
pound was dried and recrystallized from chloroform and
after concentration gives the orange product. Yield: 59%:
m.p. 128–130 ꢁC; IR (m, cmÀ1): 492 (Sb–C), 3094 (C–H aro-
matic). FAB+ m/z: 668 (20%) [M]+, 633 (6%) [M–Cl]+, 590
(62%) [MÀClÀNMe2]+, 545 (7%) [MÀClÀ2NMe2],
411(26%) [MÀFcCHMeNMe2]+, 378 (13%) [SbFcCHMe-
4. Supplementary materials
CCDC 628777, 628778, and 628779 contain the supple-
mentary crystallographic data for 1, 2, and 3. These data
can be obtained free of charge via http://www.ccdc.cam.a-
c.uk/conts/retrieving.html, or from the Cambridge Crystal-
lographic Data Centre, 12 Union Road, Cambridge CB2
1EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@
ccdc.cam.ac.uk.
Acknowledgements
The authors are thankful to DGAPA (IN210905) for
financing projects and one of the authors J.V. is thankful
to DGAPA for PD fellowship.
1
NMe2]+, 257(83%) [FcCHMeNMe2]+; H NMR (CDCl3,
d in ppm): 1.16 (d, JHH = 6.6 Hz, 3H, H3C–CH), 1.76 (d,
JHH = 6.8 Hz, 3H, H3C–CH), 1.93 (s, 6H, NMe2), 2.42
(s, 6H, NMe2), 4.08 (m, 1H, CH–H3C), 4.13 (s, 5H, CH,
C5H5), 4.17 (m, 1H, CH–H3C), 4.21 (m, 3H, CH, C5H3),
4.26 (s, 5H, CH, C5H5, and 2H, CH, C5H3), 4.36 (m, 1H,
CH, C5H3); 13C NMR (CDCl3, d in ppm): 8.4 (CH3),
15.7 (CH3), 38.9 (NMe2), 39.9 (NMe2), 60.0 (CH), 61.5
(CH), 67.5 (CH, C5H3), 67.8 (CH, C5H3), 68.4 (CH,
C5H3), 69.3 (CH, C5H5), 69.4 (CH, C5H3), 69.8 (CH,
C5H5), 70.5 (CH, C5H3), 74.1 (CH, C5H3), 79.8 (C–Sb),
84.8 (C–Sb), 96.0 (C, C5H3).
References
[1] T. Murafuji, T. Mutoh, K. Satoh, K. Tsunenari, N. Azuma, H.
Suzuki, Organometallics 14 (1995) 3848.
[2] M. Weinman, A. Gehrig, B. Schiemenz, G. Huttner, B. Nuber, G.
Reiwald, H. Lang, J. Organomet. Chem. 563 (1998) 3147.
[3] Y. Takaguchi, A. Hosowaka, S. Yamada, J. Motoyoshishya, H.
Aoyama, J. Chem. Soc., Perkin Trans. 1 (1998) 5299.
[4] D.A. Atwood, A.H. Cowley, J. Ruiz, Inorg. Chim. Acta 198–200
(1992) 271.
[5] H. Suzuki, T. Murafuji, Y. Matano, N. Azuma, J. Chem. Soc.,
Perkin Trans. 1 (1993) 2969.
´
[6] P. Sharma, D. Perez, N. Rosas, A. Cabrera, A. Toscano, J.
Organomet. Chem. 691 (2006) 579.
3.2.4. Synthesis of iodo-(N,N-dimethylaminoethyl-
ferrocenyl)(2-vinylferrocenyl)stibine (4)
[7] P. Sharma, D.A. Castillo, N. Rosas, A. Cabrera, E. Gomez, A.
Toscano, F. Lara, S. Hernandez, G. Espinosa, J. Organomet. Chem.
689 (2004) 2583.
[8] C.J. Carmalt, A.H. Cowley, R.D. Culp, R.A. Jones, S. Kamepalli,
N.C. Norman, Inorg. Chem. 36 (1997) 2770.
[9] T. Tokunaga, H. Seki, S. Yasuike, M. Ikoma, J. Kurita, K.
Yamaguchi, Tetrahedron (2000) 8833.
[10] T. Tokunaga, H. Seki, S. Yasuike, M. Ikoma, J. Kurita, K.
Yamaguchi, Tetrahedron Lett. 41 (2000) 1031.
In a Schlenk tube, to a solution of stibine 3 (0.73 g,
1.1 mmol) in CHCl3 (20 ml), CH3I (64 mmol) was added
with continuous stirring. The reaction was stirred for 2 h
at room temperature and the solution was concentrated
under vacuum to obtain an orange solid product, which
was isolated by filtration on a glass filter. The compound
was dried and recrystallized from chloroform. Yield: 75%;
m.p.: 105–107 ꢁC; IR (m, cmÀ1): 484 (Sb–C), 904 (alkene),
[11] H.J. Breunig, I. Ghesner, M.E. Ghesner, E. Lork, Inorg. Chem. 42
(2003) 1751.

J. Va´zquez et al. / Journal of Organometallic Chemistry 692 (2007) 3486–3491
3491
[12] L.M. Opris, A. Silvestru, C. Silvestru, H.J. Breunig, E. Lork, J.
Chem. Soc., Dalton Trans. (2003) 4367.
[13] S. Kamepalli, C.J. Karmalt, R.D. Culp, A.H. Cowley, R.A. Jones,
N.C. Norman, Inorg. Chem. 35 (1996) 6179.
[14] P. Sharma, J.G. Lopez, C. Ortega, N. Rosas, A. Cabrera, C. Alvarez,
A. Toscano, E. Reyes, Inorg. Chem. Commun. 9 (2006) 85.
[15] T. Ireland, K. Tappe, G. Grossheimann, P. Knochel, Chem. Eur. J. 8
(2002) 843.
[20] T. Hayashi, T. Mise, M. Fukushima, M. Kagotani, N. Nagashima,
Y. Hamada, A. Matsumoto, S. Kawakami, M. Konishi, K. Yamam-
oto, M. Kumada, Bull. Chem. Soc. Jpn. 53 (1980) 1138.
[21] P. Sharma, N. Rosas, A. Cabrera, A. Toscano, M.J. Silva, D. Perez,
L. Velasco, J. Perez, R. Guiterrez, J. Organomet. Chem. 690 (2005)
3286.
[22] J. Vela, P. Sharma, A. Cabrera, C. Alvarez, N. Rosas, S. Hernandez,
A. Toscano, J. Organomet. Chem. 634 (2001) 5.
[16] H.U. Blazer, Adv. Synth. Catal. 344 (2002) 17.
[17] H.L. Pederson, M. Johannsen, Chem. Commun. (1999) 2517.
[18] D.W. Slocum, C.A. Jennings, T.R. Engelmann, B.W. Rockett, C.R.
Hauser, J. Org. Chem. 36 (1971) 377.
[23] P. Sharma, A. Cabrera, N. Rosas, S. Hernandez, R. Lelagadec, J.
Valdes, J.L. Arias, Main Group Met. Chem. 21 (1998) 303.
[24] A.N. Sobolev, I.P. Romm, V.K. Belsky, E.N. Guryanova, J.
Organomet. Chem. 179 (1979) 153.
[19] N.S. Khrushcheva, O.V. Shakhova, V.I. Sokolov, Russ. Chem. Bull.,
Int. Ed. 52 (2003) 2146.
[25] P. Stepnicka, I. Cisarova, Inorg. Chem. 45 (2006) 8785.
[26] J. Emsley, The Elements, 3rd ed., Clarendon, Oxford, 1998.