Reactions of 2,3-diferrocenylcyclopropenone with methyllithium and phenyllithium

Article abstract of DOI:10.1016/j.jorganchem.2004.03.045

Reactions of 2,3-diferrocenylcyclopropenone with methyllithium and phenyllithium afford products of the nucleophilic opening of the three-membered ring, viz., α,β-unsaturated ketones (cis-3,4-diferrocenylbut-3-en-2-one and cis -2,3-diferrocenyl-1-phenylprop-2-enone) and allylic alcohols (cis-3,4-diferrocenyl-2-methylbut-3-en-2-ol and cis-1,1-diphenyl-2, 3-diferrocenylprop-2-en-1-ol). The insertion product of a methyl (diferrocenyl)vinylcarbenoid into a σ-bond of the starting compound, viz., 2,3,4-triferrocenyl-4- (1-ferrocenyl-2-oxopropyl) cyclobutenone, along with intramolecular ortho-alkylation products, viz., 2,3-diferrocenylindanone and 2,3-diferrocenyl-2-hydroxyindanone, were also isolated. X-ray diffraction data for triferrocenylcyclobutenone and 2,3-diferrocenyl-2 -hydroxyindanone are presented.

Full text of DOI:10.1016/j.jorganchem.2004.03.045

Journal of Organometallic Chemistry 689 (2004) 2395–2400
www.elsevier.com/locate/jorganchem
Reactions of 2,3-diferrocenylcyclopropenone with methyllithium
and phenyllithium
a
Elena I. Klimova , Tatiana Klimova , Simon Hernandez Ortega ,
a,
b
*
ꢀ
ꢀ
Marıana Esquivelzeta Rabell , Lena Ruız Ramırez , Marcos Martınez Garcıa
b
a
b
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
a
Universidad Nacional Autꢀonoma de Mꢀexico, Facultad de Quꢀımica, Ciudad Universitaria, Coyoacꢀan, C.P. 04510, Mꢀexico D.F., Mexico
Universidad Nacional Autꢀonoma de Mꢀexico, Instituto de Quꢀımica, Cd. Universitaria, Coyoacꢀan, C.P. 04510, Mꢀexico D.F., Mexico
b
Received 4 March 2004; accepted 31 March 2004
Abstract
Reactions of 2,3-diferrocenylcyclopropenone with methyllithium and phenyllithium afford products of the nucleophilic opening
of the three-membered ring, viz., a; b-unsaturated ketones (cis-3,4-diferrocenylbut-3-en-2-one and cis-2,3-diferrocenyl-1-phenyl-
prop-2-enone) and allylic alcohols (cis-3,4-diferrocenyl-2-methylbut-3-en-2-ol and cis-1,1-diphenyl-2,3-diferrocenylprop-2-en-1-ol).
The insertion product of a methyl(diferrocenyl)vinylcarbenoid into a r-bond of the starting compound, viz., 2,3,4-triferrocenyl-4-(1-
ferrocenyl-2-oxopropyl)cyclobutenone, along with intramolecular ortho-alkylation products, viz., 2,3-diferrocenylindanone and
2,3-diferrocenyl-2-hydroxyindanone, were also isolated. X-ray diffraction data for triferrocenylcyclobutenone and 2,3-diferrocenyl-
2-hydroxyindanone are presented.
Ó 2004 Elsevier B.V. All rights reserved.
Keywords: Ferrocene; Diferrocenylcyclopropenone; Triferrocenylcyclobutenone; Diferrocenylallylic cation; Diferrocenylcarbenoid; Three-membered
ring opening
1. Introduction
cyclopropenones bearing such substituents at the
C@CA bond as HO–, F–, etc. [4].
The interest in compounds of the cyclopropenone
series stems from the inherent polar pseudoaromatic
structures representing two mesomeric forms (1) $ (2)
[1,2] (Scheme 1), high strain energies, planarity, chemi-
cal reactivity of the cyclopropene moiety [1–3], and
possible practical applications.
Cyclopropenones are ambident compounds, which
react with nucleophilic, electrophilic, and bipolar
reagents and with compounds with high densities of
p-electronic systems [4].
Current chemical literature contains numerous pub-
lications devoted to the synthesis and investigations into
chemical properties of aryl- and alkyl-substituted cy-
clopropenones, their hetero-analogs incorporating
Group 15 and Group 16 elements (S, Se, N, P), and
Ferrocenyl-substituted cyclopropenones have not vir-
tually been studied so far. 2,3-Diferrocenylcycloprope-
none (3) was first isolated in low yield (ꢀ7%) in 1975 [5] by
low-temperature alkylation of ferrocene with tetrachlo-
rocyclopropene in the presence of AlCl3. Later, this
method has been improved, which allowed preparation of
2,3-diferrocenylcyclopropenone (3) in virtually quanti-
tative yield [6,7]. The availability and stability of com-
pound 3 allowed studies on its chemical transformations.
It was found that 2,3-diferrocenylcyclopropenone (3)
easily underwent three-membered ring opening to give
cis-2,3-diferrocenylacrylic acid derivatives [6] (Scheme 2).
cis-3,4-Diferrocenyl-2-methylbut-3-en-2-ol (5) was
isolated as the main reaction product with methylli-
thium [6]. It is noteworthy that compounds 4 and 5
comprising functional groups together with the ferro-
pcenyl; residues at the double bond have gained prom-
inence by virtue of their exciting structure, chemical
reactivity, and potential use as molecular building
* Corresponding author. Tel./fax: +525-622-5371.
E-mail address: klimova@servidor.unam.mx (T. Klimova).
0022-328X/$ - see front matter Ó 2004 Elsevier B.V. All rights reserved.
doi:10.1016/j.jorganchem.2004.03.045

2396
E.I. Klimova et al. / Journal of Organometallic Chemistry 689 (2004) 2395–2400
Bright-violet compound 7 was obtained as an indi-
vidual diastereomer in ꢀ8% yield. Its structure followed
O
O
1
from spectroscopic data. Thus its H NMR spectrum
contained signals for four unsubstituted cyclopentadie-
nyl rings of the ferrocene units together with signals for
substituted cyclopentadienyl fragments and singlets for
the methyl and methine groups. The 13C NMR spectrum
contained signals for four ipso carbon atoms of the
ferrocenyl fragments, two carbonyl carbon atoms, three
carbon atoms bearing no hydrogen atoms, the methyl
and methine groups, and CH groups of the ferrocenyl
substituents. The mass spectrum of compound 7 mani-
fested the presence of a molecular ion with m/z 860, which
points to its dimeric nature and confirms its structure.
The spatial configuration of triferrocenylcyclobute-
none 7 was established by X-ray diffraction analysis of a
single crystal prepared by crystallization from dichlo-
romethane (Table 1). The general view of the molecule 7 is
shown in Fig. 1. The four-membered ring is a planar
scalene quadrangle. The C@C bond length is equal to
1
2
Scheme 1.
O
Fc
H
Fc
Nu
CONu
Fc
Fc
4
3
Nu= NH2NH2, HO, PriO,
HN
Fc
Fc
MeLi
Me
Me
+ other products
H
5
ꢁ
OH
1.370 (7) A and the sharp angle at C(42) is 81.0(4)°. The
bond angles at C(41), C(43), and C(44) are close to 90°
(91.0(5)°, 95.1(5)°, and 92.3(5)°, respectively). The lengths
of the C@O, Fe–C, and carbon–carbon bonds of the
ferrocenyl rings, as well as the geometrical parameters of
the ferrocene sandwiches are close to standard values [9].
The reaction of 2,3-diferrocenylcyclopropenone (3)
with phenyllithium results also in several products
including a; b-unsaturated ketone (8), alcohol (9), 2,3-
diferrocenylindan-1-one (10), and 2,3-diferrocenyl-2-
hydroxyindan-1-one (11) (Scheme 4).
Scheme 2.
blocks and in the realm of supramolecular chemistry as
redox switching receptors [8].
In the present paper, we report the results of a de-
tailed study on the reactions of 2,3-diferrocenylcyclop-
ropenone (3) with organolithium compounds, viz.,
methyllithium and phenyllithium.
1H and 13C NMR data suggest that compounds 8 and
9 were formed as single geometrical isomers, presum-
ably, with the cis orientation of the ferrocenyl substit-
2. Results and discussion
We have found that 2,3-diferrocenylcyclopropenone
(3) reacts with an excess of methyllithium to give a
mixture of several products, the main components being
the alcohol 5 [6], 3,4-diferrocenylbut-3-en-2-one (6), and
2,3,4-triferrocenyl-4-(1-ferrocenyl-2-oxopropyl)cyclobu-
tenone (7) (Scheme 3).
Table 1
Selected bond lengths and bond angles for compounds 7 and 11
ꢁ
Selected bond lengths, r (A)
Selected bond angles, x (°)
Compound 7
C(41)–C(42)
C(42)–C(43)
C(43)–C(44)
C(44)–C(41)
C(41)–O(1)
C(42)–C(45)
C(45)–C(46)
C(46)–C(47)
1.580(8)
1.571(8)
1.370(7)
1.466(8)
1.199(6)
1.565(8)
1.527(8)
1.479(9)
C(41)–C(42)–C(43)
C(42)–C(43)–C(44)
C(43)–C(44)–C(41)
C(44)–C(41)–C(42)
C(21)–C(42)–C(45)
C(21)–C(42)–C(43)
C(45)–C(42)–C(41)
C(1)–C(43)–C(44)
81.0(4)
The structures of compounds 6 and 7 were estab-
1
95.1(5)
92.3(5)
91.0(5)
lished based on the data from H and 13C NMR spec-
troscopy and elemental analysis (see Section 4).
115.3(5)
109.0(5)
118.7(5)
138.4(6)
Previously [6], we have demonstrated that compound
5 was formed as a single isomer with cis arrangement of
the ferrocenyl groups. Diferrocenylbutenone 6 was also
isolated as a single isomer. 1H NMR data suggest
analogous cis arrangement of the ferrocenyl groups.
Compound 11
C(46)–O(2)
C(18)–C(19)
C(18)–C(11)
C(11)–C(12)
C(12)–C(13)
C(13)–C(19)
C(13)–O(2)
C(12)–O(1)
C(12)–C(20)
1.211(7)
1.380(5)
1.519(4)
1.558(5)
1.551(5)
1.472(5)
1.197(4)
1.419(4)
1.506(5)
C(11)–C(44)–C(43)
C(18)–C(19)–C(13)
C(19)–C(13)–C(12)
C(13)–C(12)–C(11)
C(12)–C(11)–C(18)
C(11)–C(18)–C(19)
O(1)–C(12)–C(13)
O(2)–C(13)–C(19)
O(2)–C(13)–C(12)
137.6(6)
110.2(3)
105.2(3)
103.2(3)
101.7(3)
111.0(3)
109.0(3)
128.4(3)
126.3(3)
O
Fc
Fc
Fc
Fc
Fc
O
Fc
H
CH3
MeLi
CH3
+
5
+
O
Fc
Fc
6
O
3
7
Scheme 3.

E.I. Klimova et al. / Journal of Organometallic Chemistry 689 (2004) 2395–2400
2397
Fig. 1. Crystal structure of compound 7.
uents [6]. 2,3-Diferrocenylindan-1-ones (10 and 11) were
obtained as single diastereomeric forms (see Section 4).
1
The IR, H and 13C NMR spectroscopic data corrob-
orate completely the structures of compounds 8–11.
The spatial structure of 2-hydroxyindan-1-one (11)
was determined by X-ray diffraction analysis of a single
crystal prepared by crystallization from ethylene glycol
(Table 1). The overall view of molecule 11 is shown in
Fig. 2(a). The molecular packing in the crystal is pre-
sented in Fig. 2(b). According to X-ray diffraction data,
the molecule 11 contains ortho-disubstituted benzene
ring fused to a five-membered ring. The ferrocenyl
substituents in positions 2 and 3 of the five-membered
ring are trans oriented, the hydroxy and carbonyl groups
occupy adjacent positions of the five-membered ring.
The Fe–C and carbon–carbon bonds of the ferrocene
sandwiches as well as their geometrical parameters are
similar to those in related compounds [10,11].
Fig. 2. (a) Crystal structure of compound 11. (b) Crystal packing of 11.
afford enones 6 and 8. The addition of the second
molecule of the organolithium reagent to the carbonyl
groups of the enones 6 and 8 yields the alcohols 5 and 9,
respectively (Scheme 5).
The intramolecular alkylation of the phenyl fragment
in intermediates 13b or (14b) results in enolate (15b).
The insertion of the carbenoid 13a into a r-bond of the
All the reaction products 5–11 are apparently formed
as a result of three-membered ring opening in the ad-
dition products (12a,b) of the organolithium compounds
at the carbonyl group of the cyclopropenone 3 to
produce diferrocenylvinyl carbenoid intermediates
(13a,b). The latter abstract proton from the solvent to
original cyclopropenone
3 affords enolate (16a).
Scheme 4.

2398
E.I. Klimova et al. / Journal of Organometallic Chemistry 689 (2004) 2395–2400
Scheme 5.
Quenching of the reaction mixtures with water converts
all the intermediates (15b) (this can also be subjected to
simultaneous oxidation by the atmospheric oxygen) and
(16a) into the final products 7, 10 and 11.
The results obtained in quenching of the reaction of
methyllithium with 2,3-diferrocenylcyclopropenone 3
with deuterium oxide support the reaction scheme pro-
posed. No deuterium was detected in compounds 5 and 6
obtained, which suggests the abstraction of proton by the
carbenoid intermediate from the solvent. Deuterium
(45%) was present only in the cyclobutenone 7 as a result
of isomerization of the enol form 16a into the keto form 7-D.
(i) cyclopropenone recyclization with ring expansion
and formation of triferrocenylcyclobutenone and (ii)
intramolecular alkylation of the phenyl fragment in
small-ring opening intermediates leading to diferroce-
nylindanone derivatives, the former process prevailing.
4. Experimental
All the solvents were dried according to the standard
procedures and were freshly distilled before use. Column
chromatography was carried out on alumina (Brock-
1
mann activity III). The H and 13C NMR spectra were
recorded on a Unity Inova Varian spectrometer (300
and 75 MHz) for solutions in CDCl3 with Me4Si as the
internal standard. The mass spectra were obtained on
Varian MAT CH-6 instrument (EI-MS, 70 eV). An El-
emental Analysis System GmbH was used for elemental
analyses.
The following reagents were purchased from Aldrich:
tetrachlorocyclopropene, 98%; ferrocene, 98%; alumi-
num chloride, 99.88%; methyllithium (1.6 M solution in
3. Conclusion
Thus, based on the results obtained one may con-
clude that the reactions of 2,3-diferrocenylcycloprope-
none (3) with organolithium compounds involve
nucleophilic opening of the cyclopropenone ring into
differicenylvinyl carbenoids leading to linear products
(the main process) and several side processes such as

E.I. Klimova et al. / Journal of Organometallic Chemistry 689 (2004) 2395–2400
2399
diethyl ether); phenyllithium (1.9 M solution in cyclo-
hexane–diethyl ether); deuterium oxide, 100.00 atom% D.
The X-ray diffraction patterns were recorded on a
Siemens P4/PC/x diffractometer (compound 7) and a
Bruker Smart Apex CCD area detector/x diffractome-
ter (compound 11). The crystallographic data, the ex-
perimental conditions, and corrections are given in
Tables 1 and 2.
2,3-Diferrocenylcyclopropenone (3) was prepared by
alkylation of ferrocene with tetrachlorocyclopropene
in the presence of AlCl3 as described in [6], the yield
was 86%, orange crystals, m.p. 182–183 °C (lit. [6]: m.p.
182–183 °C).
126 °C; alcohol 5, orange crystals, yield 2.7 g (60%),
m.p. 132–133 °C (lit. [6]: m.p. 132–133 °C); cyclobute-
none (7), violet crystals, yield 0.35 g (8%), m.p. 287–288
°C (decomp.).
cis-3,4-Diferrocenyl-2-methylbut-3-en-2-one (6): 1H
NMR: d 2.55 (3H, s, CH3), 4.04 (5H, s, C5H5), 4.06 (5H,
s, C5H5), 4.22 (4H, m, C5H4), 4.28 (2H, m, C5H4), 4.40
(2H, m, C5H4), 7.20 (1H, s, CH@). 13C NMR: 27.48
(CH3); 67.78, 69.90, 70.83, 70.86 (2C5H4); 69.23, 69.46
(2 C5H5); 79.44, 79.67 (2CipsoFc); 137.88 (CH@); 135.48
(C); 198.35 (C@O). Anal. Calc. for C24H22Fe2O: C,
65.79 H, 5.06; Fe, 25.50. Found: C, 65.56; H, 5.23; Fe,
25.71%. MS: m/z 438 [M]þ.
2,3,4-Triferrocenyl-4-(1-ferrocenyl-2-oxopropyl)cyclo-
butenone (7): 1H NMR: d 2.73 (3H, s, CH3), 4.00 (5H, s,
C5H5), 4.07 (5H, s, C5H5), 4.19 (5H, s, C5H5), 4.22 (5H,
s, C5H5), 3.31 (1H, s, CH), 3.93 (1H, m, C5H4), 3.96
(1H, m, C5H4), 4.09 (2H, m, C5H4), 4.17 (1H, m, C5H4),
4.23 (2H, m, C5H4), 4.33 (1H, m, C5H4), 4.36 (2H, m,
C5H4), 4.44 (1H, m, C5H4), 4.48 (1H, m, C5H4), 4.50
(1H, m, C5H4), 4.75 (1H, m, C5H4), 4.90 (1H, m, C5H4),
4.94 (1H, m, C5H4). 13C NMR: d 31.52 (CH3); 58.82
(CH); 67.32, 67.40 (2C), 67.63, 68.41, 68.57, 68.66 (2C),
68.84, 69.13, 69.23, 70.47, 70.54, 70.91 (2C), 71.45
(4C5H4) 68.90, 69.18, 69.48, 69.93 (4C5H5); 72.43 (C);
73.04, 74.82, 80.29, 89.70 (4CipsoFc); 140.01, 167.99
(2C); 187.86, 206.25 (2C@O). Anal. Calc. for
4.1. Reaction of 2,3-diferrocenylcyclopropenone (3) with
methyllithium
A 1.6 M solution of methyllithium in diethyl ether
(40.0 ml) was added with stirring in an inert atmosphere
to a solution of the cyclopropenone 3 (4.2 g, 10 mmol) in
dry benzene (200 ml). The mixture was stirred for 3 h at
ambient temperature and then water (100 ml) was ad-
ded. The organic layer was separated, washed with wa-
ter (2 ꢁ 50 ml), the solvent was removed in vacuo, and
the residue was chromatographed on alumina (hexane–
diethyl ether, 3:1). The following products were isolated:
enone 6, red powder, yield 0.75 g (17%), m.p. 125–
Table 2
Crystal data, data collection and refinement parameters for compounds 7 and 11
Data
7
11
1
2
Molecular formula
Formula weight (g molꢃ1
Temperature (K)
Crystal system
C47H40Fe4O2
860.19
C29H24Fe2O2 ꢂ C2H6O2
)
547.22
291(2)
Triclinic
291(2)
Monoclinic
ꢂ
Space group
ꢁ
P21=c
12.740(3)
P1
7.8714(6)
a (A)
ꢁ
b (A)
11.478(3)
25.279(5)
12.7243(10)
12.7392(10)
ꢁ
c (A)
a (°C)
b (°C)
c (°C)
90.0
101.71(2)
72.491(2)
78.003(2)
90.0
3619.8(15)
81.526(2)
1185.31(16)
3
ꢁ
V (A )
Z
4
1.578
2
1.533
Dcalc: (Mg mmꢃ3
)
Absorption coefficient (mmꢃ1
)
1.612
1768
1.255
566
F ð000Þ
ꢁ
Radiation, k (A)
Monochromator
Mo Ka, 0.71073
Graphite
Mo Ka, 0.71073
Graphite
h range (°)
1.96–25.01
6682
1.70–25.00
9760
Reflections collected
Reflections independent
Rint
6373
0.0617
4179
0.0522
Final R indices ½I > 2rðIÞꢄ
R indices (all data)
Data/restraints/parameters
Refinement method
Goodness-of fit
R1 ¼ 0:0527, wR2 ¼ 0:0601
R1 ¼ 0:1515, wR2 ¼ 0:0742
6373/0/479
Full-matrix-least-squares on F 2
0.743
R1 ¼ 0:0469, wR2 ¼ 0:0984
R1 ¼ 0:0684, wR2 ¼ 0:1044
4179/0/312
Full-matrix-least-squares on F 2
0.913
ꢃ3
ꢁ
Minimum/maximum residual electron density (e A
)
)0.329/0.387
)0.513/0.707

2400
E.I. Klimova et al. / Journal of Organometallic Chemistry 689 (2004) 2395–2400
1
C47H40Fe4O2: C, 65.62; H, 4.69; Fe, 25.97. Found: C,
65.79; H, 4.45; Fe, 26.11%. MS: m/z 860 [M]þ.
2,3-Diferrocenyl-2-hydroxyindanone (11): H NMR:
d 3.12 (1H, bs, OH), 4.15 (5H, s, C5H5), 4.20 (5H, s,
C5H5), 3.89 (1H, m, C5H4), 3.93 (1H, m, C5H4), 4.10
(1H, m, C5H4), 4.12 (2H, m, C5H4).
1
Compound 7-D: H NMR: d 2.72 (3H, s, CH3), 4.01
(5H, s, C5H5), 4.07 (5H, s, C5H5), 4.18 (5H, s, C5H5),
4.23 (5H, s, C5H5), 3.30 (0.55H, bs, CH), 3.94 (1H, m,
C5H4), 3.97 (1H, m, C5H4), 4.09 (2H, m, C5H4), 4.16
(1H, m, C5H4), 4.20 (2H, m, C5H4), 4.33 (1H, m, C5H4),
4.35 (2H, m, C5H4), 4.44 (1H, m, C5H4), 4.47 (1H, m,
C5H4), 4.50 (1H, m, C5H4), 4.73 (1H, m, C5H4), 4.89
(1H, m, C5H4), 4.93 (1H, m, C5H4).
4.19 (1H, m, C5H4), 4.26 (1H, m, C5H4), 4.28 (1H, m,
C5H4), 4.56 (1H, s, CH), 7.48 (1H, m, C6H4), 7.71–7.86
(3H, m, C6H4). 13C NMR: d 52.80 (CH); 66.14, 66.43,
67.82, 67.90, 68.09, 68.15, 68.48, 70.20 (2C5H4); 68.92,
68.94 (2C5H5); 81.06 (C); 88.11, 92.15 (2CipsoFc); 124.54,
127.27, 128.59, 135.01 (C6H4); 134.46, 137.10 (2Cipso);
182.91 (C@O). Anal. Calc. for C29H24Fe2O2: C, 67.47;
H, 4.69; Fe, 21.64. Found: C, 67.26; H, 4.77; Fe, 21.45%.
MS: m/z 516 [M]þ.
4.2. Reaction of 2,3-diferrocenylcyclopropenone (3) with
phenyllithium
A 1.9 M solution of phenyllithium in a cyclohexane–
diethyl ether mixture (35.0 ml) was added with stirring
in an inert atmosphere to a solution of the cycloprope-
none 3 (4.2 g, 10 mmol) in dry benzene (200 ml). The
mixture was stirred for 3 h at ambient temperature and
then water (100 ml) was added. The organic layer was
separated, washed with water (2 ꢁ 50 ml), the solvent
was removed in vacuo, and the residue was chromato-
graphed on alumina (hexane–diethyl ether, 2:1). The
following products were isolated: enone 8, red powder,
yield 0.8 g (16%), m.p. 147–148 °C; alcohol 9, orange
powder, yield 3.1 g (55%), m.p. 163–164 °C; indanone
10, yellow crystals, yield 0.55 g (11%), m.p. 129–131 °C;
2-hydroxyindanone 11, yellow crystals, yield 0.26 g
(5%), m.p. 171–172 °C.
5. Supplementary material
Crystallographic data for the structural analysis have
been deposited with the Cambridge Crystallographic
Data Centre, CCDC No. 232039 for compound 7 and
No. 232040 for compound 11. Copies of this informa-
tion may be obtained free of charge from The Director,
CCDC, 12 Union Road, Cambridge CB2 IEZ, UK (fax:
+44-1223-336033; e-mail: deposit@ccdc.cam.ac.uk or
www: http://www.ccdc.cam.ac.uk).
Acknowledgements
This work was supported by the grant CONACyT
cis-2,3-Diferrocenyl-1-phenylprop-2-enone (8): 1H
NMR: d 4.22 (5H, s, C5H5), 4.26 (5H, s, C5H5), 4.09
(2H, m, C5H4), 4.12 (2H, m, C5H4),4.18 (2H, m, C5H4),
4.36 (2H, m, C5H4), 7.08 (1H, s, CH@), 7.11–7.48 (5H,
m, C6H5). Anal. Calc. for C29H24Fe2O: C, 69.63; H,
4.83; Fe, 22.33. Found: C, 69.84; H, 4.76; Fe, 22.51%.
MS: m/z 500 [M]þ.
~
(Mexico, Grant 34862-E). Thanks are due to O.S. Yanez
Munoz, M.L. Velasco, J. Perez, H. Rios and E.R.
~
~
Patino, for their technical assistance.
References
cis-1,1-Diphenyl-2,3-diferrocenylprop-2-en-1-ol (9):
1H NMR: d 3.89 (5H, s, C5H5), 3.93 (5H, s, C5H5), 3.69
(2H, m, C5H4), 4.01 (2H, m, C5H4), 4.08 (2H, m, C5H4),
4.34 (2H, m, C5H4), 5.67 (1H, bs, OH), 6.02 (1H, s,
CH@), 7.30–7.53 (10H, m, 2C6H5). 13C NMR: d 68.40,
68.56, 69.68, 71.25 (2 C5H4); 68.87, 69.34 (2C5H5);
81.50, 83.71 (2CipsoFc); 83.42 (C); 127.18 (CH@); 127.74,
128.51, 133.19 (2C6H5); 136.27 (C); 147.01 (2Cipso).
Anal. Calc. for C35H30Fe2O: C, 72.69; H, 5.92; Fe,
19.32. Found: C, 72.86; H, 5.73 Fe, 19.47%. MS: m/z 578
[M]þ.
2,3-Diferrocenylindanone (10): 1H NMR: d 4.10 (5H,
s, C5H5), 4.19 (5H, s, C5H5), 3.84 (1H, m, C5H4), 3.98
(1H, m, C5H4), 4.14 (2H, m, C5H4), 4.17 (2H, m, C5H4),
4.20 (1H, m, C5H4), 4.23 (1H, m, C5H4), 4.48 (1H, d,
CH, J ¼ 3:3 Hz), 4.60 (1H, d, CH, J ¼ 3:3 Hz), 7.36–
7.70 (4H, m, C6H4). Anal. Calc. for C29H24Fe2O: C,
69.63; H, 4.84; Fe, 22.33. Found: C, 69.81; H, 4.63; Fe,
22.47%. MS: m/z 500 [M]þ.
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