1-Allylgermatrane. Synthesis, Structure and Reaction with Diazomethane

Article abstract of DOI:10.1515/znb-1997-0106

Reaction of allyltribromogermarie (2), readily available from dibromo(1,4-dioxane)germanium(II) (1) and allylbromide, with tris(2-tributylstannoxyethyl)-amine (4) gives 1-allylgermatrane (3) in almost quantitative yield. 3 crystallizes from n-pentane as a colourless crystalline solid which was characterized by ¹H and ¹³C NMR spectroscopy and by an X-ray crystal structure study. The atrane skeleton shows a strong conformational disorder; the GeN distance of 2.208(3) A suggests the presence of a coordinative Ge-N bond. Treatment of 1-allylgermatrane (3) with CH₂N₂ in the presence of catalytic amounts of Pd(OAc)₂ affords 1-cyclopropylmethylgermatrane (5) in high yield.

Full text of DOI:10.1515/znb-1997-0106

1-Allylgermatrane. Synthesis, Structure and Reaction with Diazomethane
Galina S. Zaitseva11’*, Sergey S. Karlova, Elena S. Alekseyevaa, Leonid A. Aslanova,
Evgeni V. Avtomonovb, Jörg Lorberthb *
a Chemistry Department, Moscow State University,
B-234 Vorob'evy Gory, 119899 Moscow, Russia
b Fachbereich Chemie, Philipps-Universität Marburg,
Hans-Meerwein-Strasse, D-35032 Marburg/Lahn. Germany
Z. Naturforsch. 52 b, 30-34 (1997); received August 16, 1996
Germanium, Germatrane, Cyclopropanation, X-Ray, NMR Spectra
Reaction of allyltribromogermane (2), readily available from dibromo(l,4-dioxane)ger-
manium(II) (1) and allylbromide, with tris(2-tributylstannoxyethyl)-amine (4) gives 1-
allylgermatrane (3) in almost quantitative yield. 3 crystallizes from /7-pentane as a colourless
crystalline solid which was characterized by 'H and ,3C NMR spectroscopy and by an X-ray
crystal structure study. The “atrane” skeleton shows a strong conformational disorder; the Ge-
N distance of 2.208(3) A suggests the presence of a coordinative Ge-N bond. Treatment of
1 -allylgermatrane (3) with CH2N2 in the presence of catalytic amounts of Pd(OAc)2 affords
1-cyclopropylmethylgermatrane (5) in high yield.
Introduction
molecule: at the silicon-carbon bond, the silicon-
oxygen bonds of the “atrane” fragment, and the
carbon-carbon double bond of the allylie moiety [7].
On the other hand, the chemical and struc-
tural behaviour of germanium analogues has not
been studied in detail. Only two reactions of 1-
allylgermatrane (3) have been reported and in both
cases only cleavage of the Ge-C bond took place:
Interaction of 3 with polyhaloalkanes affords 1-
halogermatranes [8], and the reaction of 3 with io-
dine gives the hydroiodide of triethanolamine and a
viscous polymeric product [9].
A general approach to the construction of the met-
alatrane moiety is the transalkoxylation reaction,
viz. the interaction of trialkoxyderivatives of silicon
and germanium with tris(2 -hydroxyalkyl)amines
[1, 2]. An alternative method involving organo-
tin reagents has been used less frequently: It
M etalatranes N(CH2CHRO)3MX (M = Si, Ge)
are of great current interest not only from the the-
oretical point of view as neutral pentacoordinated
metal species, where the nature of the M -N bond
is the object of interest [1 - 3 ] , but also due to
the marked biological activity [1, 4, 5]. Our re-
cent research has focussed on metalatranes (M =
Si, Ge) containing a functionality near to the silicon
and germanium atoms [6]. For preparative purposes
we studied the reactions of 1 -alkenylmetalatranes
which involve participation of the carbon-carbon
double bond and proceed with retention of the met-
alatrane fragment and the metal-carbon bond.
In this paper we describe the synthesis of 1-
allylgermatrane (3), the results of an X-ray inves-
tigation and the cyclopropanation reaction of this
compound by treatment with diazomethane.
comprises the reaction of trihalosilanes and
-
germanes with trialkylstannyl derivatives of tris(2-
hydroxyalkyl)amines [1 ],
Results and Discussion
For the preparation of 1-allylsilatranes we used
both methods mentioned above [10]. The use of
organotin compounds proved to be a very power-
ful synthetic route which gives the desired prod-
ucts in almost quantitative yields. It offers, how-
ever, no significant advantage as compared to the
transalkoxylation reaction that does not involve
toxic tin reagents.
1-Allylsilatranes and their reactivity have been
the subject of much recent research work. As a re-
sult of these attempts information has been obtained
regarding three possible reaction centers in this
* Reprint requests to Prof. Dr. J. Lorberth
or Dr. G. S. Zaitseva.
0939-5075/97/0100-0030 $ 06.00 (c) 1997 Verlag der Zeitschrift für Naturforschung. All rights reserved.
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G. S. Zaitseva et al. • 1-Allylgermatrane. Synthesis, Structure and Reaction with Diazomethane
31
2(EtO)3SH,
o
GeBr4
-Hs
-
2 (EtO)3SiBr
Scheme 1.
as
a
catalyst was shown to be effective
[6d, 10]. In our previous work we used
the CH2N2/Pd(OAc)2 system for the cyclo-
propanation of 1-vinylsilatrane, 1-vinyl-3,7,10-
trimethylsilatrane [6d], 1 -allylsilatrane and 1 -allyl-
3,7,10-trimethylsilatrane [10]. For comparison, the
reaction with diazomethane in the presence of
Pd(OAc)2 and without this catalyst was also ex-
plored for vinyl and allyltriethoxysilanes. The re-
actions strongly depend on the nature of the silyl
substituents and on the position of the carbon-
carbon double bond. In the case of vinyltriethoxysi-
lane and vinyl- and allylsilatranes reactions with
the CH2N2/Pd(OAc)2-system are very efficient and
gave cyclopropyltriethoxysilane, cyclopropylsila-
tranes [6d] and cyclopropylmethyl-silatranes [10 ] in
high yields. In contrast, the cyclopropanation of al-
lyltriethoxysilane in the presence of Pd(OAc)2 pro-
ceeds only in a yield of 15%. In the absence of the
catalyst, vinylsilatrane and allyltriethoxy silane do
not react with CH2N2, whereas vinyltriethoxysilane
and CH2N2 readily undergo a 1,3-cycloaddition to
give 3-triethoxysilyl-l-pyrazoline [6d]. These re-
sults have prompted us to investigate a cyclopropa-
nation reaction of 1-allylgermatrane. To the best of
our knowledge, up to now there has been no report
on germatranes with a cyclopropyl group.
Scheme 2.
In contrast, synthesis of 3 by using organotin
reagents is a more convenient route, although this
compound can also be prepared starting from allyl-
triethoxygermane which is very sensitive towards
hydrolysis [11]. Alkoxylation with tin derivatives
of trialkanolamines has been successfully used for
the preparation of other germatranes [12 ].
Allyltribromogermane (2) reacts readily with
N(CH2CH2 0 SnBu3)3 (5) under mild conditions to
give 1-allylgermatrane (3) in almost quantitative
yield (Scheme 1). 3 has been characterized by 'H
and l3C NMR spectroscopy. After recrystallization
from n-pentane it is obtained as colourless crystals
(m.p. 95-96°C), suitable for an X-ray diffraction
study.
The starting materials, 2 [13] and 1 [14], were
synthesized according to literature procedures.
At the beginning of our work in this
field only two metalatranes containing
clopropyl group, viz. 1 -cyclopropyl- and l-(2-
chlorocyclopropyl)silatrane [15, 16], were known.
These compounds were obtained via
alyzed (NaOMe) transalkoxylation reaction. l-(2-
bromocyclopropyl)-, l-(methylcyclopropyl)- and 1 -
(2-silatranylcyclopropyl)silatrane were also synthe-
sized by this method [17].
The cyclopropanation reaction (Scheme 2) was
carried out at 0 to +5°C by adding sequentially
catalytic amounts of Pd(OAc)2 and an etheral so-
lution of diazomethane to an etheral solution of 3;
the resulting product 5 was purified by sublimation
in vacuo (yield 90%) to give a white solid (m.p.
133-135°C) which has been characterized by ele-
mental analyses and 'H , 13C NMR spectroscopy.
Signals of the methylene protons of the germatrane
a cy-
a
cat-
The reaction of 1-alkenylsilatranes with dia- skeleton appear in the 'H NMR spectrum as two
zomethane in the presence of palladium(II)acetate
markedly broadened triplets at 6 2.75 (NCH2) and
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32
G. S. Zaitseva et al. • l-Allylgermatrane. Synthesis, Structure and Reaction with Diazomethane
Table I. Crystal data and structure refinement for 3.
Table II. Selected bond lengths (A) and angles (deg) for 3.
Empirical formula
Ge(l)-OU)
Ge( 1)-0(3)
G e(l)-0(2)
Ge(l)-C(7)
G e(l)-N (l)
0(l)-G e(l)-0(3)
0(l)-G e(l)-0(2) 117.9(2)
0(3)-G e(l)-0(2) 116.9(2)
0(1)-Ge(l)-C(7) 97.8(2)
0(3)-Ge(l)-C(7)
0(2)-Ge(l)-C(7) 98.7(2)
82.10(12) C( 1)-C(4)-N( 1)
0( 1)-Ge( 1)-N( 1)
0(3)-G e(l)-N (l) 82.00(13)
1.789(3)
1.791(3)
1.793(3)
1.956(4)
2.208(3)
119.5(2)
C9H |7GeNCh
259.83
298
0(2)-Ge(l)-N ( 1)
C(7)-Ge( 1)-N( 1)
C( 1)-0( 1)-Ge( 1)
C(2)-0(2)-Ge( 1)
C(3)-0(3)-Ge( 1)
C(5)-N( 1)-C(4)
C(4A)-N(1)-C(5A)
C(6A)-N(l)-Ge(l)
C(6)-N(l)-Ge(l)
0(1)-C(1)-C(4)
81.89(13)
179.4(2)
120.7(3)
120.1(3)
120.8(3)
113.5(5)
112.3(7)
104.5(5)
105.6(4)
112.2(4)
110.2(5)
107.4(5)
Formula weight
Temperature [K]
Crystal size [mm]
Radiation
Lattice
Space group
0.50 x 0.20 x 0.10
M oKa, 0.71073 A
Monoclinic
P2,/c
a = 6.8620(10)
b = 21.3470(10)
c = 8 .0 0 1 0 ( 1 0 )
0 = 97.75(2)°
1161.3(2)
Cell dimensions [A]
97.5(2)
0(1)-C(1)-C(4A)
Volume [A3]
Z
4
C(7)-Ge( 1)-N( 1) of 179.4(2)° and the sum of angles
formed by 0 ( 1), 0(2), 0(3) and Ge( 1) of 354.4(2)°
indicate that this bipyramide is slightly distorted re-
garding its equatorial plane. The germanium atom
is shifted from this plane by 0.25 A towards carbon
atom C(7). The distance N (l)-G e(l) of 2.208(3)
A indicates the presence of a transannular coordi-
native bond which is somewhat shorter than in 1 -
ethyl- and 1-terf-butylgermatrane (2.24 A for both
compounds [18]) and longer than in germatranes
with electron withdrawing substituents at the ger-
manium atom, e. g. 1 -isothiocyanato-, 1 -brom o-and
1-menthoxygermatrane (2.08 [19], 2.09 [18], and
2.15 A [6a], respectively). The structural parame-
ters reflect the tendencies known for other germa-
tranes [18 - 20]. The higher the electronegativity of
the substituent at the central atom, the shorter the
Ge-N distance.
1.486
26.22
Dcalcd [g/cm3]
Absorption coefficient //
[cm-1]
F(000)
536
6>-Range for data collection
Index ranges
1.91° - 25.97°
- 8 < h < 8 , 0 < k < 26,
0 < / < 9
Reflections collected
Independent reflections
Data / parameters
2438
2272 [R(int) = 0.0509]
2272 / 174
1.080
0.0433,0.1096
0.0560, 0.1156
0 .0 1 0 (2 )
Goodness-of-fit on F2, Sc
R
R
,a, wR2b, [I > 2 a (I)]
1, vv/?2, (all data)
Extinction coefficient
Largest diff. peak and hole
[e /A 3]
0.905 and -0.674
a r ] = x^iFoi-iFji/EiFoi;
b vv’/?2 = [£ h < F 2-F c:)2]/[£(vv(F2)2)],/2;
c S = [ £ h ’(F2-F 2 )2 ]/[£ (n -P)]'/2.
A strong conformational disorder was found for
the “atrane” skeleton and for the allylic group in
3. The minor component of this disorder model is
drawn by open lines for the bonds and by dashed
circles for the atoms. An independent refinement of
the occupational sites of all components confirmed
the assignment to two conformations. The weaker
one has an occupancy of ca. 40%, the major com-
ponent of 60%.
3.72 (OCH2) ppm (AA’BB' spin system). In the l3C
NMR spectrum signals of the carbon atoms of the
"atrane" skeleton appear at 6 56.70 (OCH2) and
51.85 (NCH2) ppm, respectively.
NMR spectra of the reaction mixture indicate the
formation of 5 as the sole product of the reaction. In
the absence of catalyst no cyclopropanation reaction
takes place.
X-ray structure determination o f 1-allylgermatrane
Experimental
The structure of 3 has been determined by X-ray
diffractometry. The experimental data are summa-
rized in Table I, and important interatomic distances
and angles in Table II. The molecular structure of 3
is shown in Fig. 1.
Solvents were dried by standard methods and dis-
tilled prior to use. Elemental analyses were carried out
by the Microanalytical Laboratory of the Chemistry De-
partment of the Moscow State University. NMR spectra
were recorded at 25°C on Varian VXR-400 and Bruker
AC 300 spectrometers. CDCL was used as solvent and
for internal deuterium lock. Chemical shifts (Ö) of the 1H
NMR and ,?C resonances are given in ppm relative to
internal TMS. Assignments of the l3C NMR data were
The germanium atom adopts a nearly ideal trig-
onal bipyramidal coordination geometry with N (l)
and C(7) atoms in the axial and with the three oxy-
gen atoms in the equatorial positions. The angle
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G. S. Zaitseva et al. ■1-Allylgermatrane. Synthesis, Structure and Reaction with Diazomethane
33
(=CH). 113,40 (=CH2), 56.71 (OCH2), 51.66 (NCH2),
25.65 (GeCH2). EI-MS, m/z (rel. int., assign.): 220 (100%,
M+-A11), 190 (7%, M+-A11-CH20), 160 (22%, M+-A11-
2CH20), 146 (12%, M+-A11-CH20-C H 2CH20), 130(5%,
M+-A11-3CH20). Bu3 SnBr could be recovered (8.27 g,
98%) after distillation of the combined filtrates, b.p. 124-
125°C/2 Torr; lit. [21]: b.p. 115-120°C/0.1 Torr.
1-Cyclopropylmethylgermatrane <5)
A solution of diazomethane (8.0 mmol) in diethylether
(60 ml) and Pd(OAc)? (ca. 5 mg) was added dropwise
to a solution of 3 (0.2 g, 0.77 mmol) in ether (10 ml)
at 0-(+5)°C. The mixture was filtered and the solvent
evaporated in vacuo. Sublimation of the residue in vacuo
yielded 0.14 g (6 6 %) of the product, m.p. 133-135°C.
'H NMR (CDCI3 ): 6 = 0.03-0.07 (m, 2H, CH2-
cyclopropane), 0.37-0.43 (m, 2H, CH2-cyclopropane),
0.79-0.87 (m, 1H, CH-cyclopropane), 0.91 (m, 2H,
GeCH2), 2.75 (t, 6 H, NCH2), 3.72 (t, 6 H, OCH2);
I3C NMR (CDCI3 ): 6 = 56.70 (OCH2). 51.85 (NCH2),
24.62 (GeCH2), 7.03 (CH2-cyclopropane), 6.41 (CH-
cyclopropane).
Fig. 1. View of a molecule of 3 with the atomic numbering
scheme. The weaker components of disordered fragments
are drawn by open lines.
Analysis for CioHiyGeNO^ 5 (273.86)
Calcd C 43.86 H 6.99 Ge 26.51%,
Found C 43.45 H7.14 Ge 26.13%.
supported by APT experiments. Mass spectra (EI-MS)
were recorded on a Varian CH-7a device using electron
impact with an ionization energy of 70 eV; all assign-
ments were made with reference to the most abundant
isotopes.
Compound 2 was obtained according to the literature
procedure [13] by refluxing a mixture of GeBr2 dioxane
(1 ) and allylbromide.
'H NMR (CDC13): 6 = 5.75 (m, 1H, =CH), 4.90 (m,
2H, =CH2), 3.11 m (2H, GeCFb). 13C NMR (CDCI3 ): 6
= 127.54 (=CH), 121,47 (=CH2), 41.62 (GeCH2). 1 was
prepared according to the published method by reacting
GeBr4 with triethoxysilane in boiling dioxane [14],
X-ray crystal structure determination
A crystal with dimensions of ca. 0.50 x 0.20 x 0.10
mm was mounted into a glass capillary and investigated
on an Enraf-Nonius CAD4 four-circle diffractometer. The
data were corrected for Lorentz and polarization effects.
The strucure was solved by Patterson methods (DIRDIF-
94) [22] and refined anisotropically by full matrix least-
squares against F2 using SHELXL-93 software [23], Hy-
drogen atoms were included into the refinement on cal-
culated positions and refined using a riding model. The
molecules were found to be systematically disordered.
Each of the three carbon atoms surrounding the nitrogen
atom and two carbon atoms of the allylic group were
split into two positions with occupancies of 0.629(8) and
0.371(8) respectively. Crystal data and numbers perti-
nent to the structure determination are summarized in
Table I [24].
Analysis for C-tHgBriGeOi (319.81).
Calcd C 14.98 H 2.52%,
Found C 14.81 H 2.64%.
1-Allylgermatrane (3)
A solution of 2 (2.7 g, 7.6 mmol) in 10 ml of CHCI3
was slowly added to a solution of 4 (7.7 g, 7.6 .mmol) in
30 ml of CHCI3 . The reaction mixture was stirred for 4 h
and the solvent evaporated in vacuo. To the residue was
added «-pentane (20 ml). A precipitate was filtered off,
washed with «-pentane (3 x 20 ml) and dried in vacuo,
yield 1.92 g (97%) (m.p. 93-95°C); lit. [9, 11]: (m.p. 95-
96°C). Recrystallization from «-pentane gave colourless
crystals with m.p. 95-96°C.
Acknowledgements
A research grant for G. S. Z. from the Deutscher
Akademischer Austauschdienst (DAAD) and support
from the Fonds der Deutschen Chemischen Industrie
VCI for J. L., as well as from the Russian Foundation
for Basic Research under the Grant No 94-03-08418 for
S. S. K. are gratefully acknowledged. E. V. A. thanks
the Graduiertenkolleg "Metallorganische Chemie” der
Philipps-Universität Marburg for providing a doctoral fel-
lowship.
'H NMR (CDCI3 ): 6 = 5.89 (m, 1H. =CH), 4.86 (m,
2H. =CH2), 3.69 (t, 6 H, OCH2), 2.74 (t, 6 H, NCH2),
1.84 (m, 2H, GeCH2). 13C NMR (CDCI3 ): 6 = 135.01
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34
G. S. Zaitseva et al. ■1-Allylgermatrane. Synthesis, Structure and Reaction with Diazomethane
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