Synthesis and properties of tellurinic anhydride-tellurone adducts

Article abstract of DOI:10.1021/om400772d

The synthesis and characterization of stable tellurinic anhydride-tellurone adducts are reported. Treatment of aryltellurinic anhydride with diaryl tellurone gave pentacyclotelluroxane consisting of two molecules each of the starting tellurium oxides. The bulky aromatic substituents attached to the tellurium atoms efficiently prevent further aggregation and enable full characterization using multinuclear (¹H, ¹³C, and ¹²⁵Te) NMR and IR spectroscopy as well as elemental analysis. For (TipTe)₄(Tip₂Te)₂O₁₀ (3TT, Tip = 2,4,6-triisopropylphenyl), the molecular structure was unambiguously determined by an X-ray crystallographic analysis. To estimate the dissociation energies of the tellurinic anhydride-tellurone adducts, density functional theory calculations were performed, and it was found that the adducts are highly stabilized by forming a four di-μ-oxo bridge structure.

Full text of DOI:10.1021/om400772d

Note
pubs.acs.org/Organometallics
Synthesis and Properties of Tellurinic Anhydride−Tellurone Adducts
Makoto Oba,*,† Kozaburo Nishiyama,† Shinichi Koguchi,‡ Shigeru Shimada,§ and Wataru Ando§
†Department of Materials Chemistry, Tokai University, 317 Nishino, Numazu, Shizuoka 410-0395, Japan
‡Department of Chemistry, Tokai University, 4-1-1 Kitakaname, Hiratsuka, Kanagawa 259-1292, Japan
§National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan
S
* Supporting Information
ABSTRACT: The synthesis and characterization of stable tellurinic
anhydride−tellurone adducts are reported. Treatment of aryltellur-
inic anhydride with diaryl tellurone gave pentacyclotelluroxane
consisting of two molecules each of the starting tellurium oxides.
The bulky aromatic substituents attached to the tellurium atoms
efficiently prevent further aggregation and enable full character-
ization using multinuclear (1H, 13C, and 125Te) NMR and IR
spectroscopy as well as elemental analysis. For (TipTe)4(Tip2Te)2O10 (3TT, Tip = 2,4,6-triisopropylphenyl), the molecular
structure was unambiguously determined by an X-ray crystallographic analysis. To estimate the dissociation energies of the
tellurinic anhydride−tellurone adducts, density functional theory calculations were performed, and it was found that the adducts
are highly stabilized by forming a four di-μ-oxo bridge structure.
he first syntheses of aryltellurinic acids and their
From the above background, treatment of the tellurinic
anhydride with an appropriate tellurium oxide, both of which
have bulky aromatic substituents, is expected to form a
spectroscopically characterizable adduct. In this study, we
investigated the synthesis and characterization of tellurinic
anhydride−tellurone adducts.
T
anhydrides were reported by Lederer1 and Petragnani,2
respectively. Since then, the tellurinic anhydrides have often
been used in organic synthesis as mild oxidizing agents.3
However, little is known about their structure because of their
tendency to form random oligomeric mixtures. Recently, we
succeeded in the first full characterization of diorgano tellurone,
which had also been known to exist as an ill-defined oligomer,
with the help of a bulky 2,4,6-triisopropylphenyl (Tip)
substituent.4 More recently, the second example of a well-
defined tellurone, bis(8-dimethylaminonaphthyl) tellurone, was
reported.5 The result prompted us to prepare some bulky
RESULTS AND DISCUSSION
■
In accord with the reported procedure for the synthesis of 4-
methoxyphenyltellurinic anhydride, [(4-MeOC6H4TeO)2O]n
(1A),3a,b,9b bulky aryltellurinic anhydrides 1T, 1D, and 1M,
which are all new compounds, were prepared (Scheme 1).
Because their 1H NMR spectra are too complex to be used for
their structural identification, the structures were confirmed by
combustion analyses.
1
aryltellurinic anhydrides (vide infra); however, their H NMR
spectra still exhibited the characteristics of oligomeric
compounds.
It is well-known that the Te−O double bond within an
organotellurium oxide is prone to dimerize to form a stable
1,3,2,4-dioxaditelluretane ring.6 For example, the X-ray crystal
structures of diaryl telluroxides, such as Ph2TeO,6a
(C6F5)2TeO,6b Tip2TeO,6c and Mes2TeO (Mes = 2,4,6-
trimethylphenyl),6c show dimeric structures with a dioxaditel-
luretane ring. The only exception is An2TeO, which forms a
linear polymeric telluroxane.7 For tellurium oxoacid derivatives,
Beckmann and co-workers reported the crystal structures of
tellurinic and telluronic acids carrying a bulky 2,6-dimesityl-
phenyl substituent, which also exist as a dimer.8 X-ray
crystallographic studies on the polymeric tellurinic anhydrides
[(8-Me2NC10H6TeO)2O]n and [(4-MeOC6H4TeO)2O]n (1A),
including a dioxaditelluretane link in the main chain, were also
reported by the same group.9 Related examples of well-defined
Te−O macrocycles involve the ionic telluroxane [Li(THF)4]-
[(i-PrTe)12O16Br4{Li(THF)Br}4Br]·2THF10 and the discrete
cluster (2-PhNNC6H4Te)6TeO11,11 which can be regarded
as the condensation product of tellurinic acids in a broad sense.
Scheme 1. Preparation of Aryltellurinic Anhydride 1
Our initial attempt to obtain the adduct of [(TipTeO)2O]n
(1T) with Tip2TeO resulted in no reaction; however, treatment
of 1T with Tip2TeO2 (2T) gave the expected adduct.
When a solution of tellurone 2T in CDCl3 was treated with
tellurinic anhydride 1T at room temperature, immediate and
Received: August 1, 2013
Published: October 18, 2013
© 2013 American Chemical Society
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Organometallics
Note
complete consumption of the starting materials and quantita-
tive formation of pentacyclotelluroxane 3TT, a 2:2 adduct of
1
1T and 2T, were observed by H NMR spectroscopic analysis.
During the process, oxidation of 1T by strongly oxidizing 2T4
was not observed, although the related partial anhydride can be
easily oxidized using H2O2.12 The obtained adduct was
chromatographically unstable, undergoing complete dissocia-
tion to 1T and 2T, which was ascertained by thin-layer
chromatography analysis. Dissociation was also observed in a
CDCl3 solution of 3TT upon addition of CD3OD. Therefore,
the adduct was isolated by triturating the concentrated reaction
mixture with hexane, yielding 62% 3TT (Table 1, entry 1). The
reaction could be conveniently performed in refluxing hexane,
from which the adduct 3TT was precipitated in a pure form in
68% yield (entry 2).
Table 1. Synthesis of Tellurinic Anhydride−Tellurone
Adduct 3
Figure 1. ORTEP plot of 3TT with 50% probability ellipsoids for the
non-hydrogen atoms. Only one orientation of the disordered p-
isopropyl in the Tip group attached to Te3 is shown.
a
b
entry
Ar in 1
Ar′ in 2
conditions
amt of 3 (%)
1
2
3
4
5
6
7
8
9
Tip (1T)
Tip (2T)
CDCl3, room temp
hexane, reflux
hexane, reflux
hexane, reflux
hexane, reflux
hexane, reflux
CHCl3, room temp
CHCl3, reflux
CHCl3, reflux
62 (3TT)
68 (3TT)
63 (3TD)
stituents are radially arranged around the core ring and
effectively prevent further aggregation. All of the Tip groups are
oriented perpendicular to the plane of the core ring system in
an alternating up-and-down arrangement. Consequently, one
ortho isopropyl group of each Tip substituent is located in the
Tip (1T)
Tip (1T)
Dep (1D)
Dep (1D)
Dep (2D)
An (2A)
c
nr
Tip (2T)
Dep (2D)
50 (3DT)
cd
,
nr
66 (3DD)
1
e
shielding region of the adjacent Tip moieties. In fact, the H
Mes (1M)
An (1A)
Tip (2T)
Tip (2T)
cm
e
NMR signals of relevant methyl groups resonate at high field
from −0.12 to 0.20 ppm. This characteristic 1H NMR spectrum
of 3TT did not change in the temperature range 23−100 °C in
toluene-d8, indicating that the solution structure of 3TT is
essentially similar to that in the solid state and is thermally
stable.
cm
a
All reactions were performed for a few minutes until the starting
materials were dissolved completely. Isolated yield. No reaction.
Probably due to low solubility of the starting materials. Complex
mixture even after overnight reaction.
b
c
d
e
The geometries around the Te(VI) atoms (Te1 and Te4) are
octahedral and are defined by four O atoms and two C atoms.
Considering the lone pair of electrons at the Te(IV) atom, the
geometries around Te2, Te3, Te5, and Te6 are trigonal
bipyramidal with the O3C donor set. The bond angles of
anhydride linkages (Te2−O9−Te6 = 120.9(2)° and Te3−
O10−Te5 = 120.8(2)°) are slightly smaller than those reported
for 1A (125.6(3)°)9b and the related (An2TeO)n (126.0(3)°),7
probably due to the ring structure.
Similar treatment of 1T with bis(2,6-diethylphenyl)tellurone
(Dep2TeO2, 2D) gave the corresponding adduct 3TD in 63%
yield (entry 3); however, no such reaction was observed
between 1T and oligomeric An2TeO2 (2A) (entry 4).
For the reaction of [(DepTeO)2O]n (1D) with 2T and 2D,
the corresponding adducts 3DT and 3DD were obtained in
50% and 66% yields, respectively. On the other hand, the
reaction of the sterically less hindered tellurinic anhydrides 1M
and 1A, having a Mes and an An group, respectively, with 2T
gave a complex mixture, and the expected adduct could not be
detected.
The structures of tellurinic anhydride−tellurone adducts 3
were confirmed by 1H, 13C, and 125Te NMR, IR, and elemental
analysis. For 3TT, we obtained a single crystal suitable for X-ray
analysis. Figure 1 shows the crystal structure of 3TT,13 which
consists of two molecules each of tellurinic anhydride 1T and
tellurone 2T. Each Te−O double bond of one tellurone is
associated with one Te−O double bond of a different tellurinic
anhydride to form a spiro[3.3]heptane ring, and another Te−O
double bond of each tellurinic anhydride is associated with
another tellurone in a similar way to furnish a pentacyclo-
[9.1.1.1.1,31.5,717,9]hexadecane structure. The eight Tip sub-
The 125Te NMR spectra of adducts 3 show two resonances
around 800 and 1390 ppm, as shown in Table 2; they are
assigned to Te(VI) and Te(IV), respectively, in accord with an
approximate integral ratio of 1:2. The chemical shift values of
Table 2. 125Te NMR Chemical Shifts of 3 in CDCl3
a
a
3
δTe(VI) (ppm)
δTe(IV) (ppm)
3TT
3TD
3DT
3DD
800
797
797
779
1392
1394
1388
1396
a
Tip2TeO (δTe 1319 ppm) was used as an external standard.
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Organometallics
Note
Te(IV) are comparable with those of the structurally related
tellurinic acid dimer [2,6-Mes2C6H3Te(O)OH]2 (δTe 1403
ppm).8a
Figure 2 shows a schematic illustration of the inorganic
telluroxane core with the bond lengths. Each dioxaditelluretane
rather retarded owing to the bulkiness and high stability of the
adduct.
In summary, we successfully prepared stable adducts of
tellurinic anhydrides with tellurones with the help of bulky
aromatic substituents, which could be fully characterized by 1H,
13C, and 125Te NMR and IR spectroscopy as well as elemental
analysis. For 3TT, the molecular structure was unambiguously
confirmed by X-ray crystallography. The dissociation energies
of 3TT and 3DD were estimated by theoretical calculations,
and the adducts were found to be highly stabilized by
constructing a pentacyclic telluroxane structure containing
four dioxaditelluretane rings.
EXPERIMENTAL SECTION
■
The melting points were determined using a Yamato MP-21 melting
point apparatus in open capillaries and are uncorrected. H, 13C, and
1
125Te NMR spectra were measured on a Varian Mercury plus 400
spectrometer at 400, 100, and 126 MHz, respectively. All of the
chemical shifts are reported as δ values (ppm) relative to residual
chloroform (δH 7.26), the central peak of deuteriochloroform (δC
77.00), and Mes2Te (δTe 275) unless otherwise noted; J values are
expressed in hertz. For 125Te NMR, Tip2TeO (δTe 1319) was used as a
secondary external standard. Infrared spectra were measured using a
JASCO FT/IR-4200 spectrometer. Elemental analyses were performed
using a PerkinElmer 2400 Series II Analyzer.
All reagents and solvents were of commercial grade and were used
according to supplier instructions unless otherwise mentioned. Diaryl
tellurones 2T, 2D, and 2M were prepared following the procedure
described previously.6c
Figure 2. Core structure of 3TT. All bond lengths are in Å.
ring consists of longer coordinative Te−O bonds (2.072−2.136
Å) and shorter Te−O bonds (1.914−1.938 Å), which are
intermediate between the Te−O double bond found in 2T
(1.80 Å)4 and typical single bonds (Te2−O9, Te3−O10, Te5−
O10, and Te6−O9) in 3TT (1.982−1.992 Å). The difference
between the longer and shorter Te−O bond lengths (average
0.18 Å) is smaller than those found in the crystal structures of
Ph2TeO (average 0.66 Å),6a (C6F5)2TeO (0.34 Å),6b Mes2TeO
(average 0.78 Å),6c Tip2TeO (average 0.67 Å),6c and 2,6-
Mes2C6H3Te(O)OH (0.25 Å),8a suggesting a relatively strong
di-μ-oxo linkage.
To estimate the dissociation energies of the tellurinic
anhydride−tellurone adducts, density functional theory
(DFT) calculations were performed on 3TT and 3DD at the
B3LYP/LANL2DZdp/6-31Gd level.14 For 3TT, the calcula-
tions successfully reproduced the X-ray crystal structure. The
calculated vibrational frequencies of 3TT and 3DD assigned to
the Te−O bond stretching in 400−700 cm−1 are in good
agreement with the experimental frequencies (see the
Supporting Information), also ensuring the reliability of the
calculations. We compared the molecular energies of the
adducts with those of the corresponding tellurinic anhydrides
and tellurones; the dissociation energies of 3TT and 3DD were
calculated to be 319.9 and 399.0 kJ/mol, respectively. These
adducts are considered to be highly stabilized by the
construction of a four di-μ-oxo bridge structure.
Preparation of Tellurinic Anhydride−Tellurone Adducts 3.
For example, a suspension of 1T (353 mg, 0.497 mmol) and 2T (283
mg, 0.500 mmol) in hexane (10 mL) was heated for a few minutes
until the starting materials dissolved completely. White solids
precipitated immediately. The reaction mixture was cooled, and the
solids were collected and dried under vacuum to afford the adduct
3TT (431 mg, 0.169 mmol, 68%). Recrystallization of 3TT from
AcOEt gave colorless prisms suitable for X-ray crystallography. Mp:
1
223−225 °C dec. H NMR (CDCl3): δ −0.12 (d, J = 7 Hz, 12H),
−0.06 (d, J = 7 Hz, 12H), 0.19 (d, J = 7 Hz, 12H), 0.20 (d, J = 7 Hz,
12H), 1.04 (d, J = 7 Hz, 12H), 1.05 (d, J = 7 Hz, 12H), 1.06 (d, J = 7
Hz, 12H), 1.07 (d, J = 7 Hz, 12H), 1.20 (d, J = 7 Hz, 12H), 1.31 (d, J
= 7 Hz, 12H), 1.35 (d, J = 7 Hz, 12H), 1.47 (d, J = 7 Hz, 12H), 2.63
(sep, J = 7 Hz, 4H), 2.67 (sep, J = 7 Hz, 4H), 3.45 (sep, J = 7 Hz, 4H),
3.61 (sep, J = 7 Hz, 4H), 3.78 (sep, J = 7 Hz, 4H), 5.45 (sep, J = 7 Hz,
4H), 6.56 (d, J = 2 Hz, 4H), 6.64 (d, J = 2 Hz, 4H), 6.81 (d, J = 2 Hz,
4H), 7.05 (d, J = 2 Hz, 4H). 13C NMR (CDCl3): δ 21.0, 22.9, 23.3,
23.5, 23.6, 23.8, 23.95, 23.97, 24.7, 25.3, 25.9, 27.6, 29.6, 30.1, 30.3,
32.3, 34.1, 34.2, 119.6, 123.6, 124.1, 124.6, 145.1, 149.0, 149.4, 149.9,
150.2, 150.6, 151.1, 153.3. 125Te NMR (CDCl3, Tip2TeO δ 1319): δ
800, 1392. IR (KBr, cm−1): 2959, 2927, 2866, 1462, 681, 645, 619,
448. Anal. Calcd for C120H184O10Te6: C, 56.47; H, 7.27. Found: C,
56.42; H, 7.29.
Finally, we examined the reaction of the tellurinic
anhydride−tellurone adducts with a phosphine for further
structural proof. When a 3DD solution in CDCl3 was treated
with an excess amount of Ph3P at room temperature for 6 days,
a complete conversion to Dep2Te and DepTeTeDep, along
3TD was obtained as a white powder in 63% yield. Mp: 197−198
°C dec. 1H NMR (CDCl3): δ −0.01 (d, J = 7 Hz, 12H), 0.08 (t, J = 7
Hz, 12H), 0.28 (d, J = 7 Hz, 12H), 1.04 (d, J = 7 Hz, 12H), 1.05 (d, J
= 7 Hz, 12H), 1.32 (dt, J = 7 and 7 Hz, 4H), 1.35 (d, J = 7 Hz, 12H),
1.37 (t, J = 7 Hz, 12H), 1.45 (d, J = 7 Hz, 12H), 2.55 (dt, J = 7 and 7
Hz, 4H), 2.65 (sept, J = 7 Hz, 4H), 3.01 (dt, J = 7 and 7 Hz, 4H), 3.65
(sept, J = 7 Hz, 4H), 3.91 (sept, J = 7 Hz, 4H), 4.47 (dt, J = 7 and 7
Hz, 4H), 6.56 (dd, J = 7 and 2 Hz, 4H), 6.63 (d, J = 2 Hz, 4H), 6.82
(d, J = 2 Hz, 4H), 7.01 (dd, J = 7 and 7 Hz, 4H), 7.06 (dd, J = 7 and 2
Hz, 4H). 13C NMR (CDCl3): δ 15.9, 16.2, 22.9, 23.5, 23.8, 24.1, 26.0,
26.7, 27.5, 29.7, 32.8, 34.2, 120.1, 123.9, 128.4, 129.0, 129.2, 144.2,
146.7, 147.6, 149.3, 150.2, 152.5, 153.4. 125Te NMR (CDCl3, Tip2TeO
δ 1319): δ 797, 1394. IR (KBr, cm−1): 3049, 2957, 2931, 2868, 1456,
687, 653, 622, 440. Anal. Calcd for C100H144O10Te6: C, 52.87; H, 6.39.
Found: C, 52.81; H, 6.50.
1
with the formation of Ph3PO, was observed by H NMR
spectroscopy (Scheme 2). The obtained telluride and
ditelluride can be regarded as reduction products of tellurone
and tellurinic anhydride, respectively, although the reaction was
Scheme 2. Reaction of 3DD with Ph3P
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Organometallics
Note
3DT was obtained as a white powder in 50% yield by
recrystallization of the reaction mixture from CH2Cl2. Mp: 210−211
°C, isolated as a 2:1 complex of 3DT and 2T including four molecules
of CH2Cl2. 1H NMR (CDCl3): δ −0.08 (d, J = 7 Hz, 12H), −0.01 (d,
J = 7 Hz, 12H), 0.41 (t, J = 7 Hz, 12H), 1.10 (d, J = 7 Hz, 24H), 1.13
(d, J = 7 Hz, 12H, Tip2TeO2), 1.16 (d, J = 7 Hz, 12H), 1.21 (d, J = 7
Hz, 6H, Tip2TeO2), 1.41 (d, J = 7 Hz, 12H), 1.44 (t, J = 7 Hz, 12H),
1.59 (dt, J = 7 and 7 Hz, 4H), 2.69 (sept, J = 7 Hz, 4H), 2.88 (dt, J = 7
and 7 Hz, 4H), 2.88 (sept, J = 7 Hz, 1H, Tip2TeO2), 3.12 (dt, J = 7
and 7 Hz, 4H), 3.30 (sept, J = 7 Hz, 4H), 3.51 (dt, J = 7 and 7 Hz,
4H), 4.09 (sept, J = 7 Hz, 2H, Tip2TeO2), 5.41 (sept, J = 7 Hz, 4H),
6.54 (d, J = 2 Hz, 4H), 6.63 (dd, J = 8 and 1 Hz, 4H), 6.84 (dd, J = 8
and 1 Hz, 4 H), 6.97 (dd, J = 8 and 8 Hz, 4H), 7.05 (d, J = 2 Hz, 4H),
7.14 (s, 2H, Tip2TeO2). 13C NMR (CDCl3): δ 14.9, 17.4, 21.6, 23.6
(Tip2TeO2), 23.8, 23.8 (Tip2TeO2), 23.9, 24.3, 24.6, 25.5, 25.8, 28.6,
29.5, 29.9, 32.8 (Tip2TeO2), 34.0, 34.3 (Tip2TeO2), 123.3, 124.0,
124.8 (Tip2TeO2), 125.6, 127.9, 129.2, 138.0 (Tip2TeO2), 144.9,
147.4, 149.0, 149.5, 150.3, 150.5, 151.2, 152.3 (Tip2TeO2), 154.8
(Tip2TeO2). 125Te NMR (CDCl3, Tip2TeO δ 1319): δ 797, 1388. IR
(KBr, cm−1): 3040, 2958, 2928, 2867, 1459, 679, 645, 606, 442. Anal.
Calcd for C234H342O22Cl8Te13: C, 51.57; H, 6.33. Found: C, 51.53; H,
6.58.
ACKNOWLEDGMENTS
■
Financial support from Tokai University is gratefully acknowl-
edged. We thank Enago (www.enago.jp) for the English
language review.
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12H), 1.35 (t, J = 7 Hz, 12H), 1.38 (t, J = 7 Hz, 12H), 1.78 (dq, J = 7
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5.29.
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signals assigned to unidentified intermediates disappeared completely,
and quantitative formation of Dep2Te, DepTeTeDep, and Ph3PO was
observed.
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(11) Srivastava, K.; Sharma, S.; Singh, H. B.; Singh, U. P.; Butcher, R.
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(12) Beckmann, J.; Bolsinger, J.; Duthie, A.; Finke, P. Organometallics
2012, 31, 289.
(13) Crystal data of 3TT: C120H184O10Te6, Mr = 2552.37, crystal
dimensions 0.18 × 0.16 × 0.09 cm3, triclinic, a = 14.8010(10) Å, b =
18.3641(13) Å, c = 25.2862(17) Å, α = 94.6230(10)°, β =
93.0820(10)°, γ = 109.7500(10)°, V = 6423.5(8) Å3, T = 153(2) K,
Theoretical Calculations. All of the calculations were performed
using the Gaussian 09 program package.14 The starting geometries
were taken from the X-ray structure of 3TT and optimized with the
DFT at the B3PW91 level. The LANL2DZdp basis set was used for
Te, whereas the 6-31G(d,p) basis set was used for C, H, and O.
Stationary points were confirmed to be minima by vibrational
frequency calculations that gave no imaginary frequencies.
space group P1 (No. 2), Z = 2, ρcalcd = 1.32 gcm−3, μ(Mo Kα) = 1.394
̅
mm−1, 38309 reflections measured, 27340 independent reflections
(Rint = 0.0239). The final R1 value was 0.0446 (I > 2σ(I)). The final
wR2(F2) value was 0.1024 (all data). The goodness of fit on F2 was
1.011. CCDC-951783 contains supplementary crystallographic data
for this compound. These data can be obtained free of charge from
The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.
uk/data_request/cif.
(14) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.;
Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci,
B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H.
P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.;
Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima,
T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.;
Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin,
K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.;
Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.;
Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.;
Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.;
Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.;
Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador,
P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.;
Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09,
Revision B.01; Gaussian, Inc., Wallingford, CT, 2010.
ASSOCIATED CONTENT
■
S
* Supporting Information
Text giving experimental details for the preparation of
aryltellurinic anhydrides 1, figures giving H, 13C, and 125Te
1
NMR and IR spectra for tellurinic anhydride−tellurone adducts
3, and a CIF file giving X-ray crystallographic data for 3TT.
This material is available free of charge via the Internet at
http://pubs.acs.org.
AUTHOR INFORMATION
■
Corresponding Author
*E-mail for M.O.: moba@tokai-u.jp.
Notes
The authors declare no competing financial interest.
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dx.doi.org/10.1021/om400772d | Organometallics 2013, 32, 6620−6623