Synthesis, characterization, and solution properties of some new organotellurium compounds based on di(cyclohexylmethyl)telluride

Article abstract of DOI:10.1002/hc.20240

A new series of organotellurium(IV) compounds based on di(cyclohexylmethyl) telluride (1) (i.e., (C₆H₁₁CH₂) ₂TeX₂ and (C₆H₁₁CH₂) ₂Te(R)X) was prepared by th

Full text of DOI:10.1002/hc.20240

Heteroatom Chemistry
Volume 18, Number 1, 2007
Synthesis, Characterization, and Solution
Properties of Some New Organotellurium
Compounds Based on
Di(cyclohexylmethyl)telluride
Ali Z. Al-Rubaie and Ala’a K. Al-Derawi
Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq
Received 29 June 2005; revised 13 January 2006
The rates of reductive elimination depended on
ABSTRACT: A new series of organotellurium(IV)
compounds based on di(cyclohexylmethyl)telluride (1)
(i.e., (C6 H CH2)2TeX2 and (C6 H CH2)2Te(R)X) was
prepared by the reaction of compound 1 with halogens,
N-bromosuccinimide, and alkyl halides. Phenylation
the nature of ionic group X [1–4]. Furthermore,
it was observed that methylation and demethylation
equilibration in dimethylsulfoxide (DMSO) is revers-
ible for methyltelluronium salts [5]. Our previous
studies of heterocyclic telluronium salts showed
that they are stable toward reductive elimination
in CHCl3, DMSO, and DMF solutions [4,6–9].
On the other hand, telluronium salts based on
2,2,6,6-tetramethyl-1-oxa-4-tellura-2,6-disilacycloh-
exane-containing benzyl or allyl groups reductively
eliminated benzyl or allyl halides in CHCl3 solutions
[10], while methyl and ethyltelluronium salts were
stable to reductive elimination [10].
In this work, we report the synthesis, solution
properties, and ligand properties for a new series
of previously unreported organotellurium(IV) com-
pounds based upon di(cyclohexylmethyl)telluride.
Furthermore, we will examine their stabilities to-
ward the reductive elimination in CDCl3 solution in
order to gain further information about their behav-
ior in solution.
11
11
of (C6 H CH2)2TeX2 with sodium tetraphenylborate
11
gave di(cyclohexylmethyl)phenyltelluronium tetraph-
enylborate in good yield. Conductivity measurements
in dimethylsulfoxide (DMSO) showed a considerable
ionic character of these compounds and they behave
as 1:1 electrolytes. 1H NMR studies in CDCl3 solution
indicated that telluronium salts employed in this study
are unstable toward reductive elimination. Reaction
of di(cyclohexylmethyl)telluride, (C6 H CH2)2Te(CH3)I ,
11
and (C6 H CH2)2Te(PhCH2)Br with HgX2 (X = Cl or
11
Br) afforded 1:1 complexes. All compounds were char-
acterized by elemental analyses and spectroscopic
ꢀ
C
data.
2007 Wiley Periodicals, Inc. Heteroatom Chem
18:93–99, 2007; Published online in Wiley InterScience
(www.interscience.wiley.com). DOI 10.1002/hc.20240
INTRODUCTION
RESULTS AND DISCUSSION
Telluronium salts of type Ph2Te(CH3)X (where
X = Cl, Br, I, NCS, PhCOO) reductively eliminate
CH3X in solvents such as chloroform and DMF.
The reaction of sodium telluride (prepared in situ
from tellurium powder and NaBH4 in aqueous
NaOH solution) with bromomethylcyclohexane gave
di(cyclohexylmethyl)telluride (1) as foul-smelling
yellow heavy oil in moderate yield. Compound 1
is soluble in common organic solvents and deposits
Correspondence to: Ali Z. Al-Rubaie; e-mail: alrubaie49@
yahoo.com.
c
ꢀ
2007 Wiley Periodicals, Inc.
93

94 Al-Rubaie and Al-Derawi
SCHEME 1 Preparative methods for compounds 1–14.
elemental tellurium during storage in a refrig-
erator for 2–3 days. Treatment of compound 1
with iodine, bromine, and chlorine in diethyl
ether gave the diiodo-, dibromo-, and dichlorotel-
lurium(IV) compounds 2, 3, and 4, respectively,
in good yields (Scheme 1). It is worth noting
that the reaction of cyanogen bromide with com-
pound 1 unexpectedly gave dibromo derivative 3
instead of di(cyclohexylmethyl)cyanotellurium bro-
mide (Scheme 1). This is in contrast to previously re-
ported works [4,11,12], and suggests that cyanogen
bromide can be used as a brominating agent in such
reactions. A 13C NMR spectrum of compound 3,
which was prepared by reacting compound 1 with
BrCN, did not show a signal corresponding to C O
(Table 1). It was also found that compound 1 read-
ily reacted with N-bromosuccinimide to form com-
pound 10 (Scheme 1, Table 1). This result agrees
well with previous works [4,13]. Compound 1 can
be easily oxidized to telluronium salts with alkyl
halides such as CH3I and C2H5Br, benzyl bromide,
2,6-dichlorobenzyl bromide, and 4-bromophenacyl
bromide to form compounds 5, 6, 7, 8, and 9, re-
spectively, in good yields (Scheme 1).
Phenylation of compound 3 was carried out in
methanol using NaBPh4 as phenylating agent and
generated compound 11 in 51% yield (Scheme 1).
Anion exchange using compounds 5, 7, and 8 as
starting materials gave the corresponding telluro-
nium salts containing the tetraphenylborate anion,
that is, compounds 12, 13, and 14, respectively
(Scheme 1). All reactions yielded pure compounds
after one recrystallization.
Molar conductivities of these compounds were
obtained in DMSO solution. Single concentration
data (10−3 M) are shown in the “Experimental” sec-
tion. The values of molar conductance approach
those expected for 1:1 electrolytes [3,4,6,8]. Com-
pounds 11, 12, 13, and 14 have low conductivi-
ties. This may be explained by the close contact be-
tween the tellurium atom and one phenyl ring of the
tetraphenylborate anion through Te–ꢀ interaction as
shown by X-ray studies on other telluronium salts
containing BPh4 anions [14,15]. The low conductiv-
ity of compound 4 may be due to the association of
this compound via ionic bonds in DMSO, since it is
well known that association is common for organ-
otellurium compounds [16,17]. The conductivities
Heteroatom Chemistry DOI 10.1002/hc

Some New Organotellurium Compounds 95
TABLE 1 1H NMR Data for Di(cyclohexylmethy)telluride Derivatives in CDCl3
Compound
R
X
Chemical Shifts (ppm); TMS = 0 ppm
1
0.7–2.0 (m, 22H, Cy H); 2.55 (d, 4H, Te CH2 Cy).
1.0–2.6 (m, 22H, Cy H); 3.70 (d, 4H, Te CH2 Cy).
1.0–2.7 (m, 22H, Cy H); 3.60 (d, 4H, Te CH2 Cy).
1.0–2.5 (m, 22H, Cy H); 3.50 (d, 4H, Te CH2 Cy).
0.8–2.1 (m, Cy H); 2.55 (da, Te CH2 Cy + CH3I ?);
3.10 (d, Te CH2 Cy); 3.50 (s, Te CH3).
2
I
I
3b
4
Br
Cl
CH3
Br
Cl
I
5
6
7
C2H5
Br
Br
0.80–2.50 (m, Cy H + Te CH2 Cy + Te CH2 CH3 +
Br CH2 CH3); 2.60–3.40 (m, Te CH2 Cy + Br CH2 CH3).
1.0–1.8 (m, Cy H); 2.35 (s, Te CH2 Ph ?); 2.55 (d, Te CH2 Cy);
2.76 (d, Te CH2 Cy ?); 4.62 (s, Br CH2 Ph);
PhCH2
7.10–7.65 (m, Ar H).
8
2,6-(Cl)2PhCH2
4-BrPhCOCH2
C4H4Oc2
Br
Br
Br
1.0–2.0 (m, Cy H); 2.55 (s, Te CH2 Cy); 3.10 (d, Te CH2 Cy);
4.23 (s, Te CH2 Ph); 4.63 (s, Br CH2 Ar); 7.00–7.70 (m, Ar H).
0.70–2.60 (m, Cy H); 3.65 (d, Te CH2 Cy); 4.40 (s, ArCO CH2 Te);
4.63 (s, ArCO CH2 Br); 7.25–8.15 (m, Ar H).
9
10
1.0–2.6 (m, 22H, Cy H); 2.97 (d, 4H, Te CH2 Cy);
2.85 (d, 4H,Te CH2 Cy); 3.37 (s, 4H, CO CH2).
0.70–1.80 (m, 22H, Cy H); 3.20 (d, 4H, Te CH2 Cy);
6.80–7.70 (m, 25H, Ar H).
0.70–1.90 (m, 22H, Cy H); 1.10 (s, 3H, Te CH3);
1.95 (d, 4H, Te CH2 Cy); 6.70–7.60 (m, 20H, Ar H).
0.70–2.30 (m, 22H, Cy H); 1.40 (d, 4H, Te CH2 Cy);
2.90 (s, 2H, Te CH2 Ph); 6.70–7.90 (m, 25H, Ar H)
0.50–1.90 (m, 22H, Cy H); 2.28 (d, 4H, Te CH2 Cy);
3.85 (s, 2H, Ar CH2 Te); 6.80–7.80 (m, 23H, Ar H).
11
12
13
14
C6H5
BPh4
BPh4
BPh4
BPh4
CH3
PhCH2
2,6-(Cl)2PhCH2
aUnsymmetrical doublet.
b13C NMR (CDCl3) for compound 3 prepared from BrCN: 18.2, 24.2, 28.2, 33.5, 46.2.
c13C NMR (CDCl3) for compound 10: 19.9, 25.4, 26.7, 28.1, 28.5, 32.9, 172.3.
of compounds 3, 5, 7, and 12 were studied as a func-
tion of concentration, that is, molar conductance
√
(ꢀM) against C, and the plots are typical of weak
electrolytes (Fig. 1).
An infrared (IR) spectrum of compound 9
showed a strong band at 1680 cm−1 corresponding
to ν(C O), while compound 10 showed two strong
bands at 1685 and 1765 cm−1 for ν(C O).
Molecular weight determinations for com-
pounds 1, 2, and 3 indicated that these compounds
are monomeric in benzene solution, and were found
to be 323.56, 580.10, and 470.00, respectively. We
were unable to determine the molecular weights of
other compounds prepared in this study because of
their insolubilities in benzene.
1H NMR data are presented in Table 1. In the
1H NMR spectra of compounds 1, 2, 3, and 4, the
expected ratios of the methylene-to-cyclohexane
protons were observed. The methylene protons
(–CH2 Te) appeared as doublets at 2.55, 3.73, 3.61,
FIGURE 1 Plot of molar conductance (ꢀM, ohm−1 cm2
√
mol−1) against C for compounds 3, 5, 7, and 12 in DMSO
solution.
Heteroatom Chemistry DOI 10.1002/hc

96 Al-Rubaie and Al-Derawi
TABLE 2 Physical and Analytical Data for Previously Unreported Hg(II) Complexes
Analysisb
H
Complexa
Color
MP (◦C)
Yield (%)
C
Tec
R2Te·HgCl2
(15)
(16)
(17)
(18)
(19)
(20)
White
Yellow
White
White
White
White
128–129
108–109
124–125
96
131–132
129
85
76
78
87
66
79
27.95 (28.33)
23.91 (24.64)
25.13 (24.49)
22.35 (21.85)
32.62 (32.99)
29.91 (29.55)
4.64 (4.42)
3.67 (3.84)
4.23 (3.97)
3.87 (3.54)
3.98 (4.35)
4.14 (3.91)
21.32 (21.50)
18.52 (18.69)
17.15 (17.35)
15.25 (15.48)
16.32 (16.69)
14.56 (14.95)
R2Te·HgBr2
R2Te(CH3)I·HgCl2
R2Te(CH3)I·HgCl2
R2Te(PhCH2)Br·HgCl2
R2Te(PhCH2)Br·HgCl2
aR = −CH2C6H11
.
bCalculated values are in parentheses.
cTellurium was analyzed according to a literature method [18].
and 3.50 ppm, respectively. The protons of cyclo-
hexane ring appeared as a complex signal between
1.0 and 2.70 ppm (Table 1). The chemical shifts of
methylene protons (i.e., –CH2 Te) for compounds
2, 3, and 4 depend on the size and electronegativity
of the halogen covalently attached to the tellurium
atom. The spectra of compounds 5–9 are complex
and show extra signals. The spectrum of compound
5 shows a singlet at 3.52 ppm, a doublet at 3.10 ppm,
an unsymmetrical doublet at 2.55 ppm, and a broad
and complex signal between 0.80 and 2.10 ppm
(Table 1). The complexity of this spectrum could be
attributed to the occurrence of reductive elimination
of these compounds in CDCl3 solution. Thus, the
unsymmetrical doublet signal could be attributed to
the sum of the doublet of Te CH2 Cy and the singlet
of CH3I. The spectrum of compound 5 was studied
as a function of time; no change was observed after
24 h and the position of methyl resonance did not
vary with time. This may indicate that alkylation
and dealkylation reactions were in equilibrium
as previously observed for other telluronium salts
attributed to the Te–ꢀ interaction between the tel-
lurium atom and one phenyl group of the BPh−4 anion
[14,15].
The reaction between equimolar quantities of
compounds 1, 5, and 7 with HgCl2 or HgBr2 afforded
1:1 complexes as white precipitates (except complex
16) (Table 2). The IR spectra of the complexes 15,
16, 17, 19, and 20 are quite similar to those of the
free ligands. The spectra of complexes 15, 17, and
19 show weak bands at 305, 310, and 310 cm−1,
respectively, which are attributed to ν(Hg Cl) [19].
The bands assigned to ν(Hg Cl) were absent in the
spectra of the bromo complexes 16, 18, and 20.
We were unable to study these complexes by NMR
spectroscopy, by conductivity measurements, or by
molecular weight determinations due their insolubil-
ities in organic solvents such as chloroform, DMSO,
or DMF. Thus, the present data do not allow a struc-
tural elucidation of these complexes and do not jus-
tify further speculation.
In conclusion, evidence was presented to suggest
that these organotellurium compounds form com-
plexes with a range of metal salts.
1
[1–5]. The H NMR spectra of compounds 6, 7, 8,
and 9 show extra signals, which may be due to the
existence of compound 1, alkyl halides, and telluro-
nium salts in the solution (Table 1). Thus, it can be
concluded that compounds 5–9 tend to eliminate
alkyl and phenacyl halides in CDCl3 solution and
equilibration took place between the telluronium
salts and di(cyclohexylmethyl)telluride and alkyl
halides, as shown in the following equation:
EXPERIMENTAL
Physical Measurements
1H NMR spectra were obtained with a Jeol EX-
90FT NMR instrument. They were recorded in CDCl3
solutions containing Me4Si as internal reference
and are reported in ꢁ units. Infrared spectra were
recorded with KBr discs in the range of 4000–
200 cmt1 on a Pye-Unicam SP-300s Infrared Spec-
trophotometer. Microanalysis for carbon, hydrogen,
and nitrogen was obtained on a Carlo-Erba EA1108
Elemental Analyzer. All melting points were deter-
mined by a Gallenkamp melting point apparatus
and are uncorrected. Molecular weight determina-
tions were carried out in benzene using KANUER
The 1H NMR spectra of compounds 11–14 show
the expected aliphatic-to-aromatic ratio. There are
no complexities or extra signals due to the reductive
elimination or to the equilibration between the re-
ducing and oxidizing forms (Table 1). This may be
Heteroatom Chemistry DOI 10.1002/hc

Some New Organotellurium Compounds 97
Cryoscopicmeter. Molar conductances at 10−3 to 10−5
M dilution in DMSO were measured with a WTW
Conductivity meter LBR, using a conductivity cell
with a cell constant of 0.69 cm−1.
sulting white crystals dried in vacuo. Yield 77.5%
(0.58 g), mp 140–142◦C.
Method B: Cyanogen bromide (0.165 g; 1.5 mmol),
compound 1 (0.5 g; 1.5 mmol), and 20 cm3 of dry
ether were placed in a flask flushed with dry nitro-
gen. An exothermic reaction took place. The mixture
was left for 1 h at room temperature. Evaporation of
solvent gave a very pale precipitate. Recrystallization
from mixture of ethanol and chloroform (4:1) gave
white crystals in 56.1% yield (0.42 g), mp 138–140◦C.
ꢀM (DMSO): 26.4 ohm−1 cm2 mol−1.
Syntheses
All experiments were carried out under pure, dry ni-
trogen. Solvents were dried and saturated with ni-
trogen and all glasswares were oven-dried and filled
with nitrogen. Bromomethylcyclohexane was pre-
pared from cyclohexylmethanol according to a lit-
erature method [20].
Anal. Calcd for C14H26TeBr2: C, 34.90; H, 5.34. Found:
C, 35.31; H, 5.19.
Di(cyclohexylmethyl)telluride (1). To a suspen-
sion of tellurium powder (4.22 g; 33 mmol) in 20%
aqueous sodium hydroxide (70 cm3) was added
sodium borohydride (3.14 g; 83 mmol) in one por-
tion. The mixture was refluxed under nitrogen atmo-
sphere for 3 h, giving a pale yellow solution of Na2Te.
To the resulting yellow solution was added a deaer-
ated solution of bromomethylcyclohexane (11.68 g;
66 mmol) in 150 cm3 of methanol. The solution was
refluxed for 5 h, and then cooled to room tempera-
ture. The solution was filtered hot, cooled to room
temperature, and extracted with diethyl ether (3 ×
100 cm3). The combined extracts were dried with an-
hydrous MgSO4. Evaporation of solvent gave a heavy
yellow oil with unpleasant odor in 58.5% yield (6.23
g).
Di(cyclohexylmethyl)tellurium dichloride (4).
Chlorine gas was slowly bubbled through a solution
of compound 1 (0.5 g; 1.5 mmol) in 20 cm3 of dry
ether with stirring for 30 min. A white precipitate
formed was filtered off, dried, and recrystallized
from ethanol/chloroform (4:1) to give white crystals
in 85% yield (0.52 g), mp 136◦C. ꢀM (DMSO): 16.3
ohm−1 cm2 mol−1.
Anal. Calcd for C14H26TeCl2: C, 42.80; H, 6.67. Found:
C, 43.27; H, 6.16.
Di(cyclohexylmethyl)methyltelluronium
iodide
(5). Excess of freshly distilled iodomethane (0.44 g;
3.1 mmol) dissolved in 10 cm3 dry ether was added to
compound 1 (0.5 g; 1.5 mmol) in 10 cm3 of dry ether.
An exothermic reaction took place. The reaction
mixture was left for 24 h at room temperature. The
white precipitate was collected by filtration, dried,
and recrystallized from ethanol. White crystals were
obtained in 79% yield (0.57 g), mp 103–104◦C. ꢀM
(DMSO): 29.6 ohm−1 cm2 mol−1.
Anal. Calcd for C15H29TeI: C, 38.83; H, 6.30. Found:
C, 39.07; H, 6.60.
The following compounds were prepared by
the reaction of the appropriate alkyl halide with
compound 1 under the conditions reported for
compound 5:
Anal. Calcd for C14H26Te: C, 52.23; H, 8.14.
Found: C, 52.05; H, 7.96.
Di(cyclohexylmethyl)tellurium diiodide (2). To a
solution of compound 1 (0.5 g; 1.5 mmol) in 10 cm3 of
dry ether was added drop by drop a solution of iodine
(0.39 g; 1.5 mmol) in 10 cm3 of dry ether. An orange
precipitate was formed immediately. The precipitate
was washed with ethanol and dried. The product was
recrystallized from ethanol/chloroform (4:1) to give
orange crystals in 84% yield (0.75 g), mp 153◦C. ꢀM
(DMSO): 36.6 ohm−1 cm2 mol−1.
Di(cyclohexylmethyl)ethyltelluronium bromide (6):
Anal. Calcd for C14H26TeI2: C, 29.20; H, 4.55.
Found: C, 30.04; H, 5.03.
White crystals, mp 100–101◦C. Yield 73% (0.49 g).
Anal. Calcd for C16H31TeBr: C, 44.55; H, 7.25. Found:
C, 44.23; H, 6.94.
Di(cyclohexylmethyl)tellurium dibromide (3).
This compound was prepared by the following two
methods:
Di(cyclohexylmethyl)benzyltelluronium bromide (7):
White crystals, mp 142◦C. Yield 87.5% (0.67 g). ꢀM
(DMSO): 26.8 ohm−1 cm2 mol−1.
Method A: To a solution of compound 1 (0.5 g; 1.5
mmol) in 10 cm3 of dry ether was added dropwise
a solution of bromine (0.25 g; 1.5 mmol) in 10 cm3
of dry ether with stirring. The pale yellow precip-
itate was filtered off, washed with ethanol, recrys-
tallized from ethanol/chloroform (1:2), and the re-
Anal. Calcd for C21H33TeBr: C, 51.16; H, 6.74. Found:
C, 51.35; H, 6.38.
Di(cyclohexylmethyl)(2,6-dichlorobenzyl)telluronium
bromide (8): White crystals, mp 135◦C. Yield 81%
(0.71 g). ꢀM (DMSO): 25.9 ohm−1 cm2 mol−1.
Heteroatom Chemistry DOI 10.1002/hc

98 Al-Rubaie and Al-Derawi
Anal. Calcd for C21H31Cl2TeBr: C, 44.89; H, 5.56.
Found: C, 45.38; H, 5.82.
Anal. Calcd for C45H53TeB: C, 73.80 H, 7.29. Found:
C, 73.54; H, 7.22.
Di(cyclohexylmethyl)(2,6-dichlorobenzyl)telluronium
tetraphenylborate (14): This compound was prepared
by the same method reported for the preparation of
compounds 13–8 (1.41 g; 2.5 mmol) with sodium
tetraphenylborate (0.85 g; 2.5 mmol) in ethanol.
White crystals were obtained in 61% yield (1.23 g),
mp 150◦C. ꢀM (DMSO): 14.3 ohm−1 cm2 mol−1.
Di(cyclohexylmethyl)(4-bromophenacyl)telluronium
bromide (9): White crystals, mp 93◦C. Yield 54%
(0.51 g). ꢀM (DMSO): 35.1 ohm−1 cm2 mol−1.
Anal. Calcd for C22H32TeOBr2: C, 44.01; H, 5.43.
Found: C, 45.19; H, 5.65.
Di(cyclohexylmethyl)succinimidotelluronium bromide
(10): N-Bromosuccinimide (0.28 g; 3.1 mmol) was
added to di(cyclomethyl)telluride (1.0 g; 3.1 mmol)
in 20 cm3 of dry benzene. A white precipi-
tate formed after 45 min. Recrystallization from
ethanol/chloroform (1:3) gave white crystals in 93%
yield (1.45 g), mp 153–155◦C.
Anal. Calcd for C45H51TeB: C, 67.45; H, 6.41. Found:
C, 67.66; H, 6.23.
Mercury(II) complexes. These complexes were
all prepared by the reaction of HgX2 (X = Cl and Br)
with compounds 1, 5, and 7. The general method is
illustrated by the following example:
Anal. Calcd for C18H30TeNO2Br: C, 44.01; H, 5.43; N,
2.80. Found: C, 44.19; H, 5.65; N, 2.57.
Synthesis of [(C6 H11CH2)2Te.HgCl2] (15): Mer-
cury(II) chloride (0.84 g; 3.1 mmol) dissolved in
ethanol/water was added to a solution of compound
1 (1.0 g; 3.1 mmol) in 50 cm3 of DMF. The mix-
ture was stirred for 30 min and a white precipi-
tate was formed. This precipitate was washed sev-
eral times with water and ethanol, respectively, and
dried in vacuo. Complex 15 was obtained in 85%
yield (1.58 g), mp 128–129◦C.
Di(cyclohexylmethyl)phenyltelluronium tetraphenylb-
orate (11): A hot ethanolic solution of sodium
tetraphenylborate (1.70 g; 5 mmol) was added with
stirring to a solution of di(cyclohexylmethyl) tel-
lurium dibromide (2) (0.96 g; 2 mmol) in 5 cm3of
chloroform. A fine white precipitate formed immedi-
ately. The resulting mixture was heated under reflux
with stirring for an hour. The white precipitate was
collected, washed with ethanol, and dried in vacuo.
Recrystallization from DMF and water gave white
precipitate of compound 10 in 51% yield (0.74 g),
mp 131–133◦C. ꢀM (DMSO): 16.5 ohm−1 cm2 mol−1.
All Hg(II) complexes and their physical proper-
ties are shown in Table 2.
REFERENCES
Anal. Calcd for C44H51TeB: C, 73.80; H, 7.20. Found:
C, 74.20; H, 7.6.
[1] Musa, F. H.; McWhinnie, W. R. J Organomet Chem
1978, 159, 37.
[2] Dance, N. S.; McWhinnie, W. R;. Mallaki, J.; Mirzai,
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[5] Rainville, D. P.; Zingaro, R. A. Inorg Chim Acta 1984,
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Di(cyclohexylmethyl)methyltelluronium tetraphenylb-
orate (12): To (C6H11CH2)2(CH3)TeI (5) (0.92 g; 2
mmol) dissolved in 20 cm3 of hot ethanol was added
a solution of sodium tetraphenylborate (0.85 g; 2.5
mmol) in 10 cm3 ethanol. A white precipitate formed
immediately. The resulting mixture was refluxed for
15 min. The precipitate was collected by filtration
and washed with water and ethanol, respectively.
Recrystallization from DMF/H2O (1:1) gave white
crystals in 62% yield (0.82 g), mp 164–165◦C. ꢀM
(DMSO): 20.3 ohm−1 cm2 mol−1.
[8] Al-Rubaie, A. Z.; Al-Shirayada, H.; Auoob, A. I. J
Organomet Chem 1988, 356, 49.
[9] Al-Rubaie, A. Z.; Al-Najar, A. A.; Jassim, F. A. Basrah
J Sci C 1994, 12, 2.
Anal. Calcd for C39H49TeB: C, 71.38; H, 7.52. Found:
C, 71.34; H, 7.32.
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Di(cyclohexylmethyl)benzyltelluronium tetraphenylb-
orate (13): The reaction of compound 7 (1.23 g; 2.5
mmol) with sodium tetraphenylborate (0.85 g; 2.5
mmol) was carried out by the same method as de-
scribed above. White crystals were obtained in 65%
yield (1.2 g), mp 153◦C. ꢀM (DMSO): 16.7 ohm−1 cm2
mol−1.
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Heteroatom Chemistry DOI 10.1002/hc