Fluorinated tellurium(IV) azides and their precursors

Article abstract of DOI:10.1016/j.jfluchem.2004.01.017

The perfluoroaryl tellurolates C₆F₅TeLi (1) and 4-CF₃C₆F₄TeLi (2) were prepared. These intermediates were identified by NMR spectroscopy and may form, depending on the reaction conditions, either the corresponding ditellanes C₆F₅TeTeC₆F₅ (3) and CF₃C₆F₄TeTeC₆F₄CF ₃ (4) by subsequent oxidation, or in the case of 1, a telluranthrene (C₆F₄Te)₂ (5) by reaction with itself. The halogenation products of 5, (C₆F₄Te)₂F₄ (6), (C₆F₄Te)₂Cl₄ (7), (C₆F₄Te)₂Br₄ (8), as well as the azidation product (C₆F₄Te)₂(N₃)₄ (9) were synthesized. Furthermore, in pursuit of our recent work on tellurium azides, the syntheses and properties of R₂Te(N₃)₂ (R=CF₃ (10), C₆F₂H₃ (11)) and RTe(N₃)₃ (R=CF₃ (12) and C₆F₅ (13)) are reported. The crystal structures of CF₃C₆F₄TeTeC₆F₄CF ₃ (4) (C₆F₄Te)₂Br₄ (8), and (C₆F₂H₃)₂Te (N₃)₂ (11) were determined.

Full text of DOI:10.1016/j.jfluchem.2004.01.017

Journal of Fluorine Chemistry 125 (2004) 997–1005
Fluorinated tellurium(IV) azides and their precursors
a,*
a
a
¨
Thomas M. Klapotke , Burkhard Krumm , Peter Mayer ,
Dieter Naumannb, Ingo Schwaba
aDepartment of Chemistry, University of Munich (LMU), Butenandtstr. 5–13(D), D-81377 Munich, Germany
bInstitute of Inorganic Chemistry, University of Cologne, Greinstr. 6, D-50939 Cologne, Germany
Received 30 May 2003; received in revised form 8 September 2003; accepted 3 January 2004
Available online 25 March 2004
Abstract
The perfluoroaryl tellurolates C6F5TeLi (1) and 4-CF3C6F4TeLi (2) were prepared. These intermediates were identified by NMR
spectroscopy and may form, depending on the reaction conditions, either the corresponding ditellanes C6F5TeTeC6F5 (3) and CF3C6F4Te-
TeC6F4CF3 (4) by subsequent oxidation, or in the case of 1, a telluranthrene (C6F4Te)2 (5) by reaction with itself. The halogenation products of
5, ( C6F4Te)2F4 (6), (C6F4Te)2Cl4 (7), (C6F4Te)2Br4 (8), as well as the azidation product (C6F4Te)2(N3)4 (9) were synthesized. Furthermore, in
pursuit of our recent work on tellurium azides, the syntheses and properties of R2Te(N3)2 (R ¼ CF3 (10), C6F2H3 (11)) and RTe(N3)3
(R ¼ CF3 (12) and C6F5 (13)) are reported. The crystal structures of CF3C6F4TeTeC6F4CF3 (4), (C6F4Te)2Br4 (8), and (C6F2H3)2Te(N3)2 (11)
were determined.
# 2004 Elsevier B.V. All rights reserved.
Keywords: Ditellanes; Tellurium azides; Tellurolates; X-ray crystallography
1. Introduction
A furthersubject of this studyis thepreparation andproperties
ofthe first perfluoroalkyl, namely, trifluoromethyl, substituted
tellurium(IV) di- and triazides. Further reported perfluoro-
alkyl tellurium(IV) di- and trifluorides are (C2F5)2TeF2 and
C2F5TeF3 [9].
During several attempts to prepare C6F5TeTeC6F5, a side-
product containing tellurium was always present in signifi-
cant amounts, which is attributed to the high reactivity of the
initially formed tellurolate C6F5TeLi. In this report, identi-
fication, characterization, and some subsequent chemistry of
this material will be accomplished.
Although tellurium species containing perfluorinated aryl
or alkyl substituents have been known for many years and
the preparation of ditellanes can be achieved by several
routes [1,2], the synthesis of C6F5TeTeC6F5 is rather com-
plicated [3,4]. The latter was first reported in 1968 [5], but
this report was considered doubtful [3]. However, a rational
synthesis was presented, by which C6F5TeTeC6F5 is acces-
sible through irradiation. Unfortunately, this proved to be
not reproducible, thus obtaining C6F5TeTeC6F5 only in low
yields if the standard reaction procedure for aryl ditellanes
is used [4]. Nevertheless, C6F5TeTeC6F5 has been fully
characterized.
2. Results and discussion
In this work, further attempts were made in order to
achieve a reproducible route to perfluoroaryl ditellanes with
acceptable yields. The ditellane serves as the only precursor
for the corresponding tellurium(IV) trifluoride C6F5TeF3 [6].
Wewere interested inC6F5TeF3 as a possiblecandidate forthe
synthesis of a perfluoroaryl substituted tellurium(IV) triazide,
following the same strategy as outlined for (C6F5)2Te(N3)2
and other alkyl/aryltellurium(IV) diazides and triazides [7,8].
2.1. Ditellanes/telluranthrenes
Similar to the standard procedures for the preparation
of PhTeTePh for a synthesis of perfluoroaryl derivatives,
the generation of the perfluoroaryllithium species RFLi
(RF ¼ C6F5 and 4-CF3C6F4) is the first step. The insertion
of Te from finely ground tellurium powder into RFLi takes
place only to a small extent as proved with C6F5Li,
4-CF3C6F4Li or other perfluoroaryl lithiums [4,10].
* Corresponding author. Tel.: þ49-89-2180-77491;
fax: þ49-89-2180-77492.
Recently, the successful use of phosphane tellurides as
soluble tellurium sources in insertion reactions was reported.
¨
E-mail address: tmk@cup.uni-muenchen.de (T.M. Klapotke).
0022-1139/$ – see front matter # 2004 Elsevier B.V. All rights reserved.
doi:10.1016/j.jfluchem.2004.01.017

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T.M. Klapotke et al. / Journal of Fluorine Chemistry 125 (2004) 997–1005
998
I2, reflux
n-BuLi/ -70˚C
Te, -20˚C
RFH
RFLi
RFTeLi
RFTeTeRF
THF
10 mol% n-Bu3P
Scheme 1. Synthesis of perfluorinated ditellanes.
Apart from Ph3P [11], mainly t-Bu3P and n-Bu3P [12]
were used, the latter also in catalytic amounts. The synthesis
of bis[2,4,6-tris(trifluoromethyl)phenyl]ditellane using
n-Bu3PTe was claimed, but unfortunately no experimental
details and spectroscopic data were disclosed [13,14]. Thus,
we probed suitable conditions for an activation of tellurium
powder by n-Bu3P in the reaction with RFLi to form RFTeLi
(RF ¼ C6F5 (1) and 4-CF3C6F4 (2)).
(C6F4Te)2 (5). An intra- or intermolecular LiF elimination,
where two molecules of tellurolate were involved, must have
occurred. The formation of 5 could proceed either via a SNAr
mechanism involving addition and elimination steps, or
by initial cleavage of an ortho C–F bond of 1 followed
by nucleophilic attack of another molecule of 1. The latter
process can be understood as a special case of a SN1 type
reaction, the intermediate zwitterionic species possibly
being stabilized by the tellurolate acting as neighboring-
group forming a three-membered tellurirene, as suggested in
ref. [10] and references therein. The octafluorotelluranthrene
(5) can be formed by both types of reaction, leaving the
pathway uncertain. In the case of 4-CF3C6F4TeLi (2), under
the same reaction conditions, complex product mixtures
inhibited the identification and isolation of corresponding
telluranthrene derivatives, similarly to the telluranthrene
isomers identified in ref. [10].
Under reflux conditions in Et2O with 1, the telluranthrene
5 can be isolated as the main product and purified by flash
chromatography. Originally, 5 was obtained by the reaction
of 1,2-diiodo-tetrafluorobenzene with tellurium at elevated
temperatures above 300 8C, and additional purification was
only achieved by means of reduction of the tetrabrominated
derivative (C6F4Te)2Br4 [16]. The latter route, compared
with ours, is rather expensive, and the overall yield is below
5%. Our new, more convenient method (Scheme 3) produces
pure 5 in approximately 30% yield in a one-pot synthesis.
The molecular structure of 4 in the crystalline state is
shown in Fig. 1. The structural features are quite similar to
those of C6F5TeTeC6F5 [4]. The dihedral angle CTeTeC is
larger (100.7(3)8) than found in C6F5TeTeC6F5 (91.8(1)8),
probably due to the increased sterical demand of the
CF3C6F4-substituent.
Catalytic amounts of n-Bu3P and reaction times of more
than 12 h turned out to be a suitable synthetic approach to
perfluorinated tellurolates. A significant difference in the
stability of 1 and 2 was observed when diethyl ether or THF
were used as solvents. Red solutions of 1 and 2 in THF are
stable even under reflux, but very sensitive towards hydro-
lysis. They exhibit broadened 19F NMR resonances and
125Te NMR resonances at d ¼ ꢀ323 (1) and ꢀ222 ppm
(2), respectively, which is upfield relative to that of PhTeLi
(d ¼ ꢀ122 ppm), in disagreement with the trends in ref.
[15]. Oxidation of 1 and 2 with molecular oxygen did not
result (or only in very small amounts) in the formation of the
ditellanes. However, with iodine, the ditellanes RFTeTeRF
(RF ¼ C6F5 (3) and 4-CF3C6F4 (4)) were formed via the
moderately stable RFTeI intermediates (Scheme 1), which
can be detected in the NMR spectra (d125Te [CDCl3] ¼ 768
(C6F5), 781 (4-CF3C6F4)). Attempts to isolate RFTeI have
been unsuccessful so far.
The ditellanes 3 and 4 are isolated in only moderate
yields, due to the use of flash chromatography and subse-
quent fractional crystallization, and because of undesirable
side reactions (Scheme 2).
However, during the use of diethyl ether as solvent at
ꢀ20 8C, and below in the case of 1, another fluorinated tell-
urium compound was always detected in significant amounts.
This material was identified as octafluorotelluranthrene
2.2. 5l4, 10l4-Perfluorotelluranthrene derivatives
n-BuLi
C6F5Li
C6F5H
Since the telluranthrene 5 can now be prepared in
moderate yield, it was of interest to study the reactivity
of this cyclic bifunctional tellane towards halogenation. As
outlined previously for other fluoroaryl tellanes [17], the
reactions with XeF2, SO2Cl2 and Br2 give the corresponding
tetrahalogeno tellurium(IV) derivatives (C6F4Te)2F4 (6),
(C6F4Te)2Cl4 (7), and (C6F4Te)2Br4 (8). All of them show
a decreased solubility relative to that of 5 (with 6 as the least
soluble), and the only suitable solvent for NMR measure-
ments is DMSO-D6. Whereas 7 and 8 are quite stable, 6 is
highly reactive towards glass in solution and needs to be
stored at low temperatures, or in TeflonTM equipment. With
Me3SiN3, all tellurium bound fluorine atoms react readily to
the moisture-sensitive tetraazido derivative (C6F4Te)2(N3)4
(9). All halogeno derivatives (6–8) are of enormous
exc.
[n-Bu3PI]I
n-Bu3P
Te
n-BuTeLi
I2
(C6F5)2Te
C6F5TeLi (1)
-LiI
n-BuTeI
I2
-LiI
n-BuTeTeC6F5
(n-BuTe)2
(C6F5Te)2
C6F5TeI
-I2
(3)
Scheme 2. Possible reactions during the synthesis of 3.

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999
F
F
F
F
Te
Te
F
F
n-BuLi/ -70˚C
Te, -20˚C
reflux
-LiF
C6F5H
C6F5Li
C6F5TeLi
½
(5)
Et2O
10 mol% n-Bu3P
F
F
Scheme 3. Synthesis of octafluorotelluranthrene.
C8
C1
Te2
Te1
˚
Fig. 1. Molecular structure of CF3C6F4TeTeC6F4CF3 (4). Selected bond lengths (A) and angles (8): Te1ꢀTe2 2.6948(9), Te1ꢀC1 2.110(8), Te2ꢀC8
2.124(8), C1ꢀTe1ꢀTe2ꢀC8 100.7(3).
thermal stability, decomposing above 330 8C, while the
tetraazide 9 can be heated slowly to its decomposition point
at 180 8C. Although 9 does not seem to be friction sensitive,
deflagration occurs when in contact with a Bunsen flame
(Scheme 4).
In relation to 5 (d125Te ¼ 762 ppm), the 125Te NMR shifts
of the oxidized species 6–9 are observed as expected
for Te(IV) compounds, found at ca. 300 ppm lower field.
Somewhat irregular to the trends observed so far (usually the
difluorides R2TeF2 are the least shielded), the tetrabromide
8 exhibits the lowest 125Te NMR shift (d ¼ 1172 ppm in
DMSO-D6). In the 19F NMR spectra, two sets of fluorine
resonances are observed, in addition for 6 a broadened
resonance at d ¼ ꢀ63 ppm for the TeF2 moiety occurs.
Slow evaporation of a saturated solution of 8 in benzene
forms suitable single crystals. The molecular structure of
8 is depicted in Fig. 2. In a similar fashion as in acyclic
dibromotelluranes R2TeBr2 [17], the bromine atoms occupy
axial positions, while two equatorial positions at each tell-
urium center are connected to the planar ring systems. The
inner C4Te2 ring itself is planar, unlike as in the structures
of 5 or other Te(II) telluranthrenes [10,16]. In contrast
to other compounds of the type R2TeX2 [17,18], for 8, no
short secondary Te ꢁ ꢁ ꢁ Br interactions are found. The Te–Br
F
F
F
F
F
F
F
F
F
X
X
X
X
F
F
Te
Te
(5)
F
F
F
F
Te
Te
F
F
XeF2, SO2Cl2 or Br2
X = F (6), Cl (7), Br (8)
CFCl3, 0 ˚C
F
6:
+ 4 Me3SiN3
- 4 Me3SiF
F
N3
N3
N3
F
F
Te
F
F
(9)
Te
N3
F
Scheme 4. Synthesis of 5l4, 10l4-telluranthrene derivatives of 5.

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1000
Te(N3)4 (1382 ppm, DMSO-D6) by reaction of TeF4 with
Me3SiN3 [19,20].
Br2
The tellurium azides 9–13 show asymmetric stretching
vibrations (nasN3) of the azido groups, as well as intense
TeN stretching vibrations in their Raman spectra. For the
tetraazide 9, between 2100 and 2000 cmꢀ1, more than five
different peaks for nasN3 are found. Compared with
Me2Te(N3)2 [8], in (CF3)2Te(N3)2 (10) both the nasN3 and
the nTeN are shifted slightly to higher wavenumbers. The
C6
Te
C1
Te
nTeC stretching vibration, for Me2Te(N3)2 at 550 cmꢀ1
,
is not detected. Three different nasN3 (axial out of phase,
axial in phase, equatorial), are found between 2115 and
2048 cmꢀ1 for the triazides 12 and 13. In the case of
(C6F2H3)2Te(N3)2 (11), two discrete peaks for nasN3 are
visible in the Raman spectrum at 2072/2050 cmꢀ1, which is
slightly higher than found for Ph2Te(N3)2 and (C6F5)2Te(N3)2
[7].
The 125Te NMR shifts of the diazides are typically found
at slightly higher field than those of the corresponding di-
fluorides, for example d125Te ¼ 1116 (10) versus 1200 ppm
((CF3)2TeF2, CDCl3). The resonances of the triazides 12 and
13 are found at lower field compared with those of the
corresponding diazides.
Br1
˚
Fig. 2. Molecular structure of (C6F4Te)2Br4 (8). Selected bond lengths (A)
and angles (8): TeꢀBr1 2.6201(11), TeꢀBr2 2.6615(10), TeꢀC1 2.120(8),
Br1ꢀTeꢀBr2 174.60(4).
distances are almost identical to those of acyclic fluorophe-
nyltelluranes R2TeBr2 [17].
2.3. Trifluoromethyl tellurium(IV) and fluorophenyl
diazides and triazides
The bis-trifluoromethyl and the partially fluorinated bis-
2,6-difluorophenyl substituted tellurium(IV) diazides 10 and
11, as well as the trifluoromethyl and pentafluorophenyl
tellurium(IV) triazides 12 and 13 are prepared similarly
to the syntheses of the non-fluorinated analogues [8]
(Scheme 5). Compound 11 was prepared in an effort to
obtain structural data in addition to the crystal structures of
Ph2Te(N3)2 and (C6F5)2Te(N3)2 (see structure discussion).
All four compounds are yellowish moisture-sensitive solids,
10 being the most sensitive tellurium diazide regarding its
propensity to explode and hydrolyze. This is probably due
to the strong polarization effect of the CF3 group destabiliz-
ing the Na–Nb bond, leading to an increased tendency to
eliminate molecular nitrogen. The triazide CF3Te(N3)3 (12)
is even more sensitive and could not be obtained in pure form.
The pentafluorophenyl derivative C6F5Te(N3)3 (13) was
obtained in a mixture with (C6F5)2Te(N3)2 and Te(N3)4.
The intermediate C6F5TeF3, formed by fluorination of 3,
is known to dismutate even at low temperatures into
(C6F5)2TeF2 and TeF4 [6]. Upon treatment with Me3SiN3,
the corresponding azides were formed. Both species in
this mixture have been unambiguously identified by their
125Te NMR shifts by comparison with authentic samples in
DMSO-D6. The diazide (C6F5)2Te(N3)2 (916 ppm, DMSO-
D6) was prepared according to [7], and the tetraazide
A cold solution in CH2Cl2/hexane led to nearly colorless
crystals of 11 suitable for X-ray crystal structure analysis.
The difference in the sterical arrangements of Ph2Te(N3)2
and (C6F5)2Te(N3)2, the orientation of the azide groups, was
discussed in terms of steric reasons and electrostatic repul-
sions between free electron pairs of fluorine and nitrogen [7].
In the case of 11, the same orientation of the substituents as
in Ph2Te(N3)2 is found (see Fig. 3a), although it does not
ꢀ
crystallize isotypically (11: P1, Ph2Te(N3)2: Pbca). In both
11 and Ph2Te(N3)2 the azide groups, located in the axial
positions, are oriented towards the aryl groups. The opposite
was found for the structure of (C6F5)2Te(N3)2. That means,
an increased electronegativity of C6F2H3 compared with
C6H5 because of the introduction of two fluorine atoms in
the ortho position, does not lead to a significant change in the
orientation of the azide groups. The tellurium nitrogen
˚
distances are Te–N1 2.228(2) and Te–N4 2.202(2) A, which
are also very similar to those found in Ph2Te(N3)2. The
intermolecular Te ꢁ ꢁ ꢁ N interactions (Te ꢁ ꢁ ꢁ N4 2.970(2),
˚
Te ꢁ ꢁ ꢁ N1 3.287(2) A) found in the three-dimensional struc-
ture of 11 (Fig. 3b), are shorter than in the case of
˚
Ph2Te(N3)2 (Te ꢁ ꢁ ꢁ N 3.141/3.497 A), and cause in principle
the same connectivity pattern (Te ꢁ ꢁ ꢁ NaꢀTe, but in
(C6F5)2Te(N3)2: Te ꢁ ꢁ ꢁ Ng ꢁ ꢁ ꢁ Te, no Te ꢁ ꢁ ꢁ Na).
Me3SiN3
(RF)2TeF2
(RF)2Te(N3)2
RF = CF3 (10), C6F2H3 (11)
RF = CF3 (12), C6F5 (13)
CFCl3, 0 ˚C
1. XeF2 / 2. Me3SiN3
RFTeTeRF
RFTe(N3)3
CFCl3, 0 ˚C
Scheme 5. Synthesis of fluorinated tellurium(IV) diazides and triazides.

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T.M. Klapotke et al. / Journal of Fluorine Chemistry 125 (2004) 997–1005
1001
F1
N1
N2
N3
Te
F2
N4
N5
N6
F3
F4
(a)
N1(i)
Te(ii)
N1(ii)
Te(i)
N4(i)
N4(ii)
Te
N4
N1
(b)
˚
Fig. 3. (a) Molecular structure of (C6F2H3)2Te(N3)2 (11). Selected bond lengths (A) and angles (8): Te–N1 2.228(2), Te–N4 2.202(2), Te–C1 2.113(2), Te–C7
2.106(3), C–F 1.350(3)–1.362(3), N1–N2 1.213(3), N2–N3 1.142(3), N4–N5 1.229(3), N5–N6 1.136(3), N1–Te–N4 167.71(8), C1–Te–C7 106.56(10), N1–
˚
N2–N3 177.5(3), N4–N5–N6 177.1(3). (b) Te ꢁ ꢁ ꢁ N interactions in the structure of (C6F2H3)2Te(N3)2 (11). Selected contact distances (A): Te ꢁ ꢁ ꢁ N1 (i)
3.287(2), Te ꢁ ꢁ ꢁ N4 (ii) 2.970(2); with i ¼ 1 ꢀ x, 1 ꢀ y, 1 ꢀ z; ii ¼ ꢀx, 1 ꢀ y, 1 ꢀ z.
It can be concluded, that the arrangement of the azide
groups is not due to electronic or steric reasons, because both
effects are present, to substantial extents, in the two ortho-
difluorophenyl substituents as well. Therefore, the change in
orientation as found in (C6F5)2Te(N3)2 can probably be
explained by packing effects.
literature [21,22]. Solvents were dried by standard methods
[23], distilled and stored over molecular sieves. Raman spec-
tra were recorded on a Perkin-Elmer 2000 NIR FT-Raman
spectrometer fitted with a Nd-YAG laser (1064 nm), infrared
spectra on a Perkin-Elmer 983G IR spectrometer between
KBr plates. Mass spectroscopic data were obtained from a
JEOL Mstation JMS 700 Spektrometer with fragments refer-
ring to the nuclei with the highest abundance (for example
130Te). The elemental analyses were performed with a C, H,
N-Analysator Elementar Vario EL. NMR spectra were
recorded on a JEOL Eclipse 400 instrument, and chemical
shifts are with respect to (CH3)4Si (1H, 13C), CH3NO2 (14N),
CFCl3 (19F), and Me2Te (125Te). Melting points were deter-
3. Experimental
3.1. General procedures
All manipulations of air and moisture-sensitive materials
were performed under an inert atmosphere of dry nitrogen or
argon using flame-dried glass vessels and Schlenk techni-
ques. Xenon difluoride (FluoroChem) and trimethylsilyl
azide (Aldrich) were used as received. The compounds
(CF3)2TeF2 and CF3TeTeCF3 were prepared according to the
mined in capillaries using a Buchi B540 instrument.
¨
CAUTION: Covalent tellurium azides are potentially
explosive; appropriate safety precautions such as Kevlar
gloves, face shield, leather jacket must be taken, and the
amounts of substance handled in pure form by trained

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T.M. Klapotke et al. / Journal of Fluorine Chemistry 125 (2004) 997–1005
1002
personnel should not exceed 100 mg. During the prepara-
tion of (CF3)2Te(N3)2 (10) once a vigorous explosion
occurred, destroying the glass vessel completely. The yields
and elemental analyses of the azides 9 and 10 were not
determined due to safety reasons.
were added slowly. After 1.5 h, 25 mmol of finely ground
tellurium powder and 2.5 mmol n-Bu3P were added. The
dark suspension was slowly warmed to ꢀ20 8C and held for
approximately 15 h at this temperature. After additional
refluxing for 2.5 h, a yellow solution was separated from
unreacted tellurium and concentrated in vacuo. Purification
by column chromatography with petrol ether/methylene
chloride (4:1) yielded an orange solution, which was
concentrated until crystallization occurred to give orange
crystals of 5.
3.2. Preparation of RFTeTeRF (RF ¼ C6F5 (3),
CF3C6F4 (4))
A solution of 25 mmol pentafluorobenzene or 4-trifluoro-
methyltetrafluorobenzene in ca. 30 ml THF was cooled to
ꢀ78 8C, and 27.5 mmol of n-BuLi (2.5 M in hexanes) were
slowly added with slight darkening of the reaction solution.
After 1.5 h, 25 mmol of finely ground tellurium powder and
2.5 mmol n-Bu3P were added. The mixture was slowly
warmed to ꢀ20 8C and held for 15 h at this temperature.
Iodine (25 mmol) was added and the mixture warmed to
ambient temperature, then refluxed for 2 h. After cooling
to 20 8C again, small amounts of sulfur (0.25 mmol) were
added and the mixture was then refluxed again for 30 min.
Unreacted tellurium was separated by filtration at ambient
temperature, and the resulting solution was poured into a
solution of 25 mmol NaHSO3 in 150 ml H2O, and 150 ml of
diethyl ether were added. Drying of the organic phase over
CaCl2 and evaporation of the solvent in vacuo yielded dark
brown oils which were subjected to flash chromatography
with petrol ether/methylene chloride (10:1). The dark red
solution was concentrated in vacuo and dark red rhombic
crystals (3), or dark red needles (4), were finally separated
from the pale yellow crystals of the corresponding mono-
tellanes by fractional crystallization.
Yield: 33%, mp 122–124 8C. Raman: n ¼ 1610 (20),
1591 (20), 1483 (10), 1421 (10), 1294 (20), 1266 (40),
771 (45), 637 (15), 474 (100), 395 (20), 357 (45), 234
(70), 212 (95), 191 (35), 133 (15) cmꢀ1 19F NMR [CDCl3]:
.
d ¼ ꢀ108:0 (m, 2F, 2-F); ꢀ151.6 (m, 2F, 3-F) ppm. 13C
1
2
NMR [CDCl3]: d ¼ 148:0 (d, JCF ¼ 239:9 Hz, JCTe
¼
38:8 Hz, 3JCTe ¼ 11:9 Hz, C-2), 140.1 (d, 3JCF ¼ 253:6 Hz,
3JCTe ¼ 12:7 Hz, C-3), 111.6 (m, JCTe ¼ 332:1 Hz,
1
2JCTe ¼ 71:9 Hz, C-1) ppm. 125Te NMR [CDCl3]: d ¼ 762
3
(t, JTeF ¼ 15:9 Hz) ppm. Mass spectra, elemental analysis
and IR see also ref. [16].
3.3.1. 1,2,3,4,5,5,6,7,8,9,10,10-Dodecafluoro-5l4,
10l4-telluranthrene (6)
A solution of 2 mmol 5 in 15 ml of CFCl3 was cooled to
0 8C, and into the stirred solution, 4.2 mmol of XeF2 were
added. The yellow color disappeared immediately and a
colorless suspension was formed. After stirring for 1.5 h at
ambient temperature, a colorless residue was separated from
the supernatant.
Yield: 88%, mp 333 8C (dec.). Raman: strong fluores-
cence. IR: n ¼ 1612 m, 1603 m, 1576 m, 1523 m, 1489 vs,
1459 vs, 1370 w, 1328 w, 1316 w, 1299 w, 1272 m, 1107 s,
1027 s, 813 w, 772 w, 634 w, 619 m, 595 w, 519 m, 485 m,
C6F5TeTeC6F5 (3): yield (33%), spectroscopic data see
[3,4].
CF3C6F4TeTeC6F4CF3 (4): yield (46%), mp 92–93 8C.
Raman: n ¼ 1643 (25), 1377 (15), 917 (5), 782 (10), 718
(15), 502 (55), 444 (20), 403 (25), 310 (15), 197 (100,
nTeTe), 175 (70) cmꢀ1. IR: n ¼ 1642 m, 1597 w, 1481 vs,
1468 vs, 1414 w, 1378 w, 1351 w, 1322 vs, 1294 w, 1259 w,
1213 m, 1181 s, 1156 s, 973 s, 920 s, 782 w, 715 s, 646 w,
472 m, 424 m, 382 m, 361 m, 315 m, 296 m cmꢀ1 19F NMR
.
[DMSO-D6]: d ¼ ꢀ63 (br, 2F, TeF), ꢀ122.0 (m, 2F, 2-F),
ꢀ150.3 (m, 2F, 3-F) ppm. 13C{19F} NMR [DMSO-D6]:
d ¼ 147:3 (2JTeC ¼ 43:8 Hz, C-2), 140.7 (C-3), 130.0
(1JTeC ¼ 331:4 Hz, C-1) ppm. 125Te{19F} NMR [DMSO-
D6]: d ¼ 1112 (br) ppm. EIMS 70 eV, m/z (rel. int.) ¼
627 [Mþ] (43), 607 [Mþ–F] (24), 589 [Mþ–2F] (20),
442 [Mþ–F–TeF2] (78), 315 [Mþ–TeF–TeF2] (20), 296
[C12F8þ] (100). EA Calc. for C12F12Te2: C, 23.0. Found:
C, 23.5.
546 w, 502 w, 422 w, 307 w cmꢀ1 19F NMR [CDCl3]:
.
d ¼ ꢀ56:9 (t, 4JFF ¼ 21:7 Hz, 3F, CF3), ꢀ113.0 (m, 2F, 2-F),
ꢀ138.7 (m, 2F, 3-F) ppm. 13C NMR [CDCl3]: d ¼ 149:0
1
2
(dm, JCF ¼ 250:6 Hz, JCTe ¼ 18:9 Hz, C-2), 142.4
1
3
(dm, JCF ¼ 265:2 Hz, JCTe ¼ 16:6 Hz, C-3), 120.6
1
(q, JCF ¼ 274:8 Hz, CF3), 111.8 (m, C-4), 91.0 (tm,
2JCF ¼ 31:1 Hz, JCTe ¼ 420:1 Hz, JCTe ¼ 8:5 Hz, C-1)
3.3.2. 5,5,10,10-Tetrachloro-1,2,3,4,6,7,8,9-octafluoro-
5l4,10l4-telluranthrene (7)
1
2
ppm. 125Te NMR [CDCl3]: d ¼ 338 (tm, JTeF ¼ 65:2 Hz)
3
ppm. EIMS 70 eV, m/z (rel. int.) ¼ 689 [Mþ] (15), 670
[Mþ–F] (2), 563 [Mþ–Te] (50), 347 [CF3C6F4Teþ] (100).
Calc. for C14F14Te2: C, 24.4. Found: C, 24.6.
A solution of 0.7 mmol 5 in 15 ml of CFCl3 was cooled to
0 8C, and into the stirred solution, 5 ml (excess) of SO2Cl2
were added. The yellow color vanished rapidly and a color-
less suspension was formed. After stirring for 4 h at ambient
temperature, the resulting mixture was evaporated in vacuo
yielding a colorless powder.
3.3. Preparation of octafluorotelluranthrene (5),
halogenation, and azidation products
Yield: 99%, mp > 345 8C (dec.). Raman: n ¼ 1615 (10),
1279 (10), 771 (15), 472 (25), 396 (20), 373 (25), 357 (25),
291 (100, nTeCl), 251 (35), 210 (43), 160 (20) cmꢀ1. IR:
A solution of 20 mmol pentafluorobenzene in ca. 30 ml
diethyl ether was cooled to ꢀ78 8C, and 22 mmol of n-BuLi

¨
T.M. Klapotke et al. / Journal of Fluorine Chemistry 125 (2004) 997–1005
1003
n ¼ 1621 m, 1600 s, 1549 w, 1501 vs, 1443 vs, 1354 w, 1318
3.4. Preparation of trifluoromethyl and fluorophenyl
tellurium di- and triazides
m, 1304 m, 1271 m, 1118 s, 1104 s, 1017 s, 827 m, 805 w,
762 m, 722 w, 636 m, 605 w, 568 w, 519 w, 470 w, 370 m,
351 w, 297 m cmꢀ1
.
19F NMR [DMSO-D6]: d ¼ ꢀ114:6 (m,
3.4.1. Bis(trifluoromethyl)diazido-l4-tellane
(CF3)2Te(N3)2 (10)
2F, 2-F), ꢀ150.9 (m, 2F, 3-F) ppm. 13C{19F} NMR [DMSO-
D6]: d ¼ 145:4 (2JCTe ¼ 40:7 Hz, C-2), 138.9 (C-3), 130.4
(1JCTe ¼ 369:0 Hz, C-1) ppm. 125Te{19F} NMR [DMSO-
D6]: d ¼ 1076 (br) ppm. EIMS 70 eV, m/z (rel. int.) ¼ 658
[Mþ–Cl] (100), 623 [Mþ–2Cl] (29), 588 [Mþ–3Cl] (55), 551
[Mþ–4Cl] (45), 426 [Mþ–Te–4Cl] (80), 404 [Mþ–Te–F–4Cl]
(25). EA Calc. for C12F8Te2Cl4: C, 20.7, Cl 20.8. Found: C,
20.7, Cl 22.0.
Into a stirred solution of 120 mg (0.4 mmol) (CF3)2TeF2 in
5 ml of CH2Cl2 were added 110 mg (0.9 mmol) Me3SiN3 at
0 8C. After 2 h of stirring, the yellow suspension was dried
for severalhoursatambienttemperatureinvacuo(10ꢀ3 mbar)
to yield a slightly yellowish, friction sensitive powder.
Mp 35 8C. Raman: n ¼ 2070 (20)/ 2025 (5, nasN3), 1328
(5), 1093 (5), 1039 (5), 743 (10), 642 (10), 355 (100, nTeN),
290 (10), 266 (10), 239 (10), 205 (10) cmꢀ1. IR: n ¼ 2144
m/2052 vs (nasN3), 1681 m, 1313 w, 1261m, 1170, 1102 m,
3.3.3. 5,5,10,10-Tetrabromo-1,2,3,4,6,7,8,9-octafluoro-5l4,
10l4-telluranthrene (8)
A solution of 0.7 mmol 5 in 15 ml of CFCl3 was cooled to
0 8C. Into the stirred solution, 150 ml (excess) of bromine
were added. The product precipitated immediately. After
stirring for 1 h at room temperature, the resulting mixture
was evaporated in vacuo, yielding a slightly yellowish
powder.
Yield: 96%, mp > 345 8C (dec.). Raman: strong fluores-
cence. 19F NMR [DMSO-D6]: d ¼ ꢀ114:0 (m, 2F, 2-F),
ꢀ150.2 (m, 2F, 3-F) ppm. 13C{19F} NMR [DMSO-D6]:
d ¼ 147:4 (2JCTe ¼ 38:4 Hz, C-2), 140.8 (C-3), 131.9
(1JCTe ¼ 386:7 Hz, C-1) ppm. 125Te{19F} NMR [DMSO-
D6]: d ¼ 1172 (br) ppm. EIMS 70 eV, m/z (rel. int.) ¼ 792
[Mþ–Br] (30), 711 [Mþ–2Br] (7), 632 [Mþ–3Br] (95), 426
[Mþ–Te–4Br] (100). Mass spectra, elemental analysis and
IR see ref. [16].
1054 s, 622 s, 527 m cmꢀ1
.
19F NMR: d ¼ ꢀ41:7
(2JFTe ¼ 133:9 Hz) [CDCl3]; ꢀ49.6 [DMSO-D6] ppm.
13C NMR: d ¼ 122:5 (1JCTe ¼ 215:6 Hz) [{19F}, CDCl3];
127.0 (1JCF ¼ 368:3 Hz) [DMSO-D6] ppm. 14N NMR, Du1/2
(Hz): d ¼ ꢀ142 (Nb, 40), ꢀ237 (Ng, 1100), ꢀ275 (Na,
1700) [CDCl3]; ꢀ139 (Nb, 120), ꢀ199 (Ng, 580), ꢀ290
(Na, >2000) [DMSO-D6] ppm. 125Te NMR: d ¼ 1116 (sept)
[CDCl3]; 1152 (m) [DMSO-D6] ppm. EIMS 70 eV, m/z (rel.
int.) ¼ 495 [CF3CF2TeTeCF2CF3þ] (8), 426 [CF3CF2Te-
TeCF2þ] (4), 337 [Te(CF3)3þ] (2), 324 [Mþ–N2] (1), 287
[(CF3)2TeFþ] (10), 283 [Mþ–CF3] (5), 282 [(CF3)2TeNþþ]
(5), 268 [(CF3)2Teþ] (10), 199 [CF3Teþ] (40), 69 [CF3
(100).
]
3.4.2. Bis(2,6-difluorophenyl)diazido-l4-tellane
(C6F2H3)2Te(N3)2 (11)
Into a solution of 0.7 mmol of (C6F2H3)2TeF2 in 5 ml of
CH2Cl2 were added 2.0 mmol of Me3SiN3 at 0 8C. After 2 h
of stirring, volatile materials were removed in vacuo, the
yellowish residue was washed with 2 ml of CH2Cl2 and
evaporated again to dryness.
Yield 78%, mp 176 8C. Raman: n ¼ 3091 (30), 2072 (25)/
2050 (20, nasN3) 1605 (10). 1464 (5), 1440 (5), 1317 (10),
1271 (15), 1154 (10), 1082 (5), 1037 (10), 753 (5), 696 (5),
646 (15), 555 (25), 378 (20), 344 (100, nTeN), 330 (50), 308
(65), 258 (15), 195 (25), 149 (25) cmꢀ1. IR: n ¼ 3084 m,
2066 s/ 2049 vs (nasN3), 2038 vs, 1604 s, 1592 s, 1580 s,
1538 w, 1468 vs, 1457 vs, 1317 m, 1261 m, 1233 s, 1151 m,
1082 m, 1034 w, 985 s, 785 s, 785 s, 753 m, 698 m, 640 br,
3.3.4. 5,5,10,10-Tetraazido-1,2,3,4,6,7,8,9-octafluoro-5l4,
10l4-telluranthrene (9)
Into a solution of 0.5 mmol of 5 in 30 ml CH3CN were
added 1.2 mmol XeF2 in one portion at 0 8C. The colorless
solution was stirred for 4 h, then 4.4 mmol of Me3SiN3 were
added, changing the color to orange during addition. After
2 h at ambient temperature, a slightly yellowish residue
had separated from the yellow solution. The mixture was
evaporated in vacuo, yielding a yellow powder.
Mp > 180 8C (dec.). Raman: n ¼ 2103 (20)/2086 (15)/
2063 (20)/2033 (20)/2003 (15, nasN3), 1607 (5), 1345 (20),
1325 (15), 1278 (15), 1024 (5), 816 (10), 771 (10), 644 (20),
600 (10), 572 (20), 547 (20), 488 (60), 472 (45), 407 (30),
373 (70), 356 (70), 331 (100, nTeN), 308 (50), 266 (50), 228
(80), 206 (55), 157 (55) cmꢀ1. IR: 2050/2037 vs (nasN3),
1621 m, 1544 w, 1489 vs, 1456 vs, 1663 w, 1327 m, 1313 m,
1271 s, 1106 s, 1042 m, 1025 s, 809 w, 769 m, 732 w, 717 w,
555 m, 535 m, 504 m cmꢀ1
.
19F NMR [CDCl3]: d ¼ ꢀ96:2/
ꢀ97.3 (m, 2F, 2-F) ppm. 13C{19F} NMR [CDCl3]:
d ¼ 162:5 (br, C2), 136.5 (C4), 134.8 (C3), 105.3 (C1)
ppm. 14N NMR [CDCl3, Du1/2 (Hz)]: d ¼ ꢀ139 (Nb, 80),
ꢀ191 (Ng, 300), ꢀ290 (Na, 1400) ppm. 125Te{1H} NMR
[CDCl3]: d ¼ 773 (m) ppm. EIMS 70 eV, m/z (rel. int.) ¼
356 [Mþ–2N3] (100), 242 [C6F2H3Teþ] (55), 226
[C12H6F4þ] (80). Calc. for C12H6N6F4Te: C, 32.9; H, 1,4;
N, 19.2. Found: C, 33.0; H, 1.3; N, 18.5.
566 m, 542 m, 470 w, 378 m, 352 w, 313 m cmꢀ1 19F NMR
.
[DMSO-D6]: d ¼ ꢀ120:5 (m, 2F, 2-F), ꢀ149.5 (m, 2F, 3-F)
ppm. 13C{19F} NMR [DMSO-D6]: d ¼ 148:0 (C-2), 141.3
(C-3), 128.0 (C-1) ppm. 14N NMR [DMSO-D6, Du1/2
(Hz)]: d ¼ ꢀ134 (Nb, 80), ꢀ165 (Ng, 300), ꢀ244 (Na, >
2000) ppm. 125Te{19F} NMR [DMSO-D6]: d ¼ 1074 (br)
ppm. DCIMS 70 eV, m/z (rel. int.) ¼ 658 [Mþ–N3] (1), 595
[Mþ–3N3] (1), 553 [Mþ–4N3] (100).
3.4.3. Trifluoromethyltriazido-l4-tellane CF3Te(N3)3 (12)
Into a stirred solution of 110 mg (0.3 mmol) CF3TeTeCF3
in 5 ml of CFCl3 were added 170 mg (1 mmol) XeF2 at 0 8C.

¨
T.M. Klapotke et al. / Journal of Fluorine Chemistry 125 (2004) 997–1005
1004
Table 1
Crystal data and structure refinements
(CF3C6F4Te)2 (4)
(C6F4Te)2Br4ꢁC6H6 (8)
(C6F2H3)2Te(N3)2 (11)
Empirical formula
Formula mass
C14F14Te2
689.33
200
C18H6Br4F8Te2
949.04
200
C12H6F4N6Te
437.81
200
Temperature (K)
Crystal size (mm)
Crystal system
Space group
0.03 ꢂ 0.09 ꢂ 0.37
Monoclinic
C2/c
0.02 ꢂ 0.10 ꢂ 0.10
Monoclinic
P21/c
0.07 ꢂ 0.20 ꢂ 0.26
Triclinic
ꢀ
P1
˚
a (A)
29.519(6)
6.1941(8)
18.932(3)
99.93(2)
11.1563(6)
7.2559(4)
15.3136(9)
111.312(2)
1154.9(1)
2
7.5448(2)
9.8636(2)
11.3422(3)
91.4537(8)a
730.08(3)
2
˚
b (A)
˚
c (A)
b (8)
3
V (A )
˚
3410(1)
Z
8
rcalc (g cmꢀ3
)
2.686
3.567
2.729
9.515
1.992
2.089
m (mmꢀ1
F(0 0 0)
)
2512
860
416
y range (8)
Index ranges
2.2–23.8
2.9–19.8
3.2–27.5
ꢀ33 ꢃ h ꢃ 33
ꢀ6 ꢃ k ꢃ 6
ꢀ19 ꢃ l ꢃ 21
9082
ꢀ10 ꢃ h ꢃ 10
ꢀ6 ꢃ k ꢃ 6
ꢀ14 ꢃ l ꢃ 14
6043
ꢀ9 ꢃ h ꢃ 9
ꢀ12 ꢃ k ꢃ 12
ꢀ14 ꢃ l ꢃ 14
11028
Reflections collected
Reflections unique
R1, wR2 (2s data)
R1, wR2 (all data)
Max./min. transm.
Data/restr./param.
GOOF on F2
2559 (Rint ¼ 0.101)
0.0512, 0.1255
0.0592, 0.1306
0.8938, 0.5806
2559/0/271
0.979
1040 (Rint ¼ 0.056)
0.0256, 0.0563
0.0342, 0.0607
0.6411, 0.3476
1040/0/145
1.190
3305 (Rint ¼ 0.046)
0.0245, 0.0569
0.0274, 0.0583
0.8923, 0.7278
3305/0/208
1.052
3
˚
Larg. Diff. peak/hole (e/A )
1.376/ꢀ2.201
0.400/ꢀ0.381
0.495/ꢀ1.151
a a ¼ 114.1008(8), g ¼ 106.2896(8)8.
After 40 min, into the turbid solution 260 mg (2.2 mmol)
Me3SiN3 at ꢀ20 8C were added and stirred for additional
15 min until the effervescence had stopped. The yellow
suspension was evaporated and dried in vacuo.
(br, 1F, 4-F), ꢀ160.0 (br, 2F, 3-F) ppm. 13C{19F} NMR
[DMSO-D6]: d ¼ 146:4 (C-2), 142.8 (C-4), 137.5 (C-3),
117.4 (br, C-1) ppm. 14N NMR [DMSO-D6, Du1/2 (Hz)]:
d ¼ ꢀ140 (Nb, 120), ꢀ230 (Ng, >2000), ꢀ260 (Na, >2000)
ppm. 125Te NMR [DMSO-D6]: d ¼ 1277 (m) ppm.
Raman: n ¼ 2115 (35)/2091 (15)/2070 (15, nasN3), 737
(15), 662 (20), 422 (100), 402 (90), 365 (65, nTeN), 278
(50), 198 (50) cmꢀ1
.
19F NMR [DMSO-D6]: d ¼ ꢀ56:0 (s)
3.5. X-ray crystallography
ppm. 13C NMR [DMSO-D6]: d ¼ 128:5 (1JCꢀF ¼ 363:8 Hz)
ppm. 14N NMR [DMSO-D6, Du1/2 (Hz)]: d ¼ ꢀ140 (Nb,
120), ꢀ230 (Ng, >2000), ꢀ260 (Na, >2000) ppm. 125Te
NMR [DMSO-D6]: d ¼ 1406 (m) ppm.
Data for compound 4 were collected on a Stoe IPDS
image plate area detector, data for compounds 8 and 11 were
collected on a Nonius Kappa CCD. Thermal ellipsoids
are shown with 50% probability. Structure solution and
refinement were performed as outlined in ref [8].
Crystallographic data (excluding structure factors) for
the structures in this paper have been deposited with the
Cambridge Crystallographic Data Centre as supplementary
publication nos. CCDC 211267 (4), 211268 (8), and 211269
(11) (Table 1). Copies of the data can be obtained, free of
charge, on application to CCDC, 12 Union Road, Cambridge
CB2 1EZ, UK, (fax: þ44-1223-336033 or e-mail: deposit@
ccdc.cam.ac.uk).
3.4.4. Pentafluorophenyltriazido-l4-tellane C6F5Te(N3)3
(13)
Into a stirred solution of 110 mg (0.2 mmol) C6F5Te-
TeC6F5 in 10 ml of CFCl3 were added 120 mg (0.7 mmol)
XeF2 at 0 8C. After 25 min, into the turbid solution 180 mg
(1.6 mmol) Me3SiN3 at 0 8C were added and stirred for
additional 10 min until the effervescence had stopped. The
brownish suspension was evaporated and dried in vacuo.
According to 19F and 125Te NMR spectra, the compounds
(C6F5)2Te(N3)2 and Te(N3)4 were present each in ca. 30%.
Raman: n ¼ 2110 (20)/2085 (30)/2048 (15, nasN3), 1639
(5), 1516 (5), 1319 (5), 1263 (5), 1088 (5), 803 (5), 648 (15),
587 (10), 536 (5), 493 (20), 418 (100), 381 (25), 341 (95,
Acknowledgements
nTeN), 310 (30), 245 (20), 222 (20), 178 (30) cmꢀ1
NMR [DMSO-D6]: d ¼ ꢀ127:6 (br, 2F, 2-F), ꢀ147.9
.
19F
Financial support of this work by the University of Munich
and the Fonds der Chemischen Industrie is gratefully

¨
T.M. Klapotke et al. / Journal of Fluorine Chemistry 125 (2004) 997–1005
1005
¨
[10] T.M. Klapotke, B. Krumm, P. Mayer, H. Piotrowski, K. Polborn,
acknowledged. We wish to thank the research students
Mr. M.B. Rauscher and Mr. B.L.J. Kindler for their strong
commitment during the preparation of some compounds. We
are also indebted to and thank Prof. P. Klu¨fers for generous
allocation of X-ray diffractometer time.
J. Fluorine Chem. 123 (2003) 133.
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Int. Engl. 28 (1989) 179.
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D. Stalke, F.T. Edelmann, New J. Chem. 23 (1999) 905.
[14] F.T. Edelmann, Comments Inorg. Chem. 12 (1992) 259.
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