Reaction of phenyltrifluorosilane and phenyl(hydrocarbyl)difluorosilanes with bis(2-hydroxyethyl)- and tris(2-hydroxyethyl)amine and their N-methyl and O-trimethylsilyl derivatives. A novel route to quasisilatranes

Article abstract of DOI:10.1134/S1070363206120024

Reaction of phenyltrifluorosilane, diphenyldifluorosilane, and methylphenyldifluorosilane with bis(2-hydroxyethyl)amine, methyl-bis(2- hydroxyethyl)amine, methyl-bis(2-trimethylsiloxyethyl)amine, leads to 1,3-dioxa-6-aza-2-silacyclooctane derivatives, (N → Si) quasisilatranes: 1,1-difluoroquasisilatrane, 1-phenyl-1-fluoro-5-methylquasisilatrane, or 1-methyl-1-fluoroquasisilatrane, containing the donor-acceptor bond N → Si and pentacoordinate silicon atom. 1-Phenylsilatrane was found to be the product of the reaction of phenyltrifluorosilane with tris(2-trimethylsiloxyethyl)amine, whereas with tris(2-hydroxyethyl)amine 1-phenylsilatrane and 1-fluorosilatrane were formed in the molar ratio of 3:1. The structure of the synthesized compounds was proved by ¹H, ¹³C, ¹⁵N, ¹⁹F, ²⁹Si NMR and IR spectroscopy.

Full text of DOI:10.1134/S1070363206120024

ISSN 1070-3632, Russian Journal of General Chemistry, 2006, Vol. 76, No. 12, pp. 1854 1859.
Original Russian Text M.G. Voronkov, A.I. Albanov, E.A. Grebneva, O.M. Trofimova, N.F. Chernov, N.N. Chipanina, 2006, published in Zhurnal
Obshchei Khimii, 2006, Vol. 76, No. 12, pp. 1942 1947.
Pleiades Publishing, Inc., 2006.
Reaction of Phenyltrifluorosilane
and Phenyl(hydrocarbyl)difluorosilanes
with Bis(2-hydroxyethyl)- and Tris(2-hydroxyethyl)amine
and Their N-Methyl and O-Trimethylsilyl Derivatives.
A Novel Route to Quasisilatranes
M. G. Voronkov, A. I. Albanov, E. A. Grebneva,
O. M. Trofimova, N. F. Chernov, and N. N. Chipanina
Favorskii Irkutsk Institute of Chemistry, Siberian Branch,
Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: voronkov@irioch.irk.ru
Received October 19, 2006
Abstract Reaction of phenyltrifluorosilane, diphenyldifluorosilane, and methylphenyldifluorosilane with
bis(2-hydroxyethyl)amine, methyl-bis(2-hydroxyethyl)amine, methyl-bis(2-trimethylsiloxyethyl)amine, leads
to 1,3-dioxa-6-aza-2-silacyclooctane derivatives, (N Si) quasisilatranes: 1,1-difluoroquasisilatrane, 1-phenyl-
1
-fluoro-5-methylquasisilatrane, or 1-methyl-1-fluoroquasisilatrane, containing the donor acceptor bond
Si and pentacoordinate silicon atom. 1-Phenylsilatrane was found to be the product of the reaction of
phenyltrifluorosilane with tris(2-trimethylsiloxyethyl)amine, whereas with tris(2-hydroxyethyl)amine
-phenylsilatrane and 1-fluorosilatrane were formed in the molar ratio of 3: 1. The structure of the synthesized
N
1
1
13
15
19
29
compounds was proved by H, C, N, F, Si NMR and IR spectroscopy.
DOI: 10.1134/S1070363206120024
Previously we have shown that the reaction of
protodesilylation of phenyltrifluorosilane with
containing pentacoordinate silicon atom and donor
acceptor bond N Si as well as its hydrofluoride (X)
with hexacoordinate silicon atom (1). Earlier we have
8
-hydroxy- or 8-mercaptoquinoline [1] or 2-hydroxy-
ethylamine and its mono- and di-N-methyl derivatives
2 5] results in new intracomplex heterocyclic com-
found that upon bubbling of gaseous SiF into the
4
[
solution of bis(2-hydroxyethyl)amine in hexane a new
bicyclic compound (N Si) 2,2-difluoro-1,3-dioxa-6-
pounds posessing pentacoordinate silicon atom.
1
9
aza-2-silacyclooctane is formed [10]. From the
F
Aiming at elaboration of new routes of synthesis
of hypervalent silicon intracomplex compounds and
29
and Si NMR data the intracomplex compounds IX
and X exist in fast equilibrium.
expansion of possibilities of using of PhSiF and
3
PhRSiF (R = Ph, Me, etc.) in organoelement syn-
2
The first step of reaction (1) is, apparently, the
rupture of the Ph Si bond with elimination of benzene
and formation of N-(2-hydroxyethyl)-N-(2-trifluoro-
siloxyethyl)amine. The intramolecular dehydrofluori-
nation of the latter results in the formation of intra-
complex compound IX. Subsequent reaction of the
latter with HF affords hydrofluoride X.
thesis [1 10], we have studied the reaction of phenyl-
trifluorosilane (I), diphenyldifluorosilane (II) and
methylphenyldifluorosilane (III) with bis(2-hydroxy-
ethyl)amine (IV), methyl-bis(2-hydroxyethyl)amine
(V), methyl-bis(2-trimethylsiloxyethyl)amine (VI),
tris(2-hydroxyethyl)amine (VII) and tris(2-trimethyl-
siloxyethyl)amine (VIII).
We consider these compounds as bicyclic analogs
of silatranes and, therefore, they could be named as
1,1-difluoroquasisilatranes. The numbers of atoms in
the ring are the same as adopted for silatranes [11, 12].
It should be mentioned that the first representatives
of quasisilatranes were obtained in the laboratory of
Reaction of PhSiF (I) with bis(2-hydroxyethyl)-
3
amine (IV) at 5 to 0 C proceeds in 20-30 min
with splitting the Ph Si bond, elimination of benzene
and formation of intracomplex bicyclic (N Si)
2
,2-difluoro-1,3-dioxa-6-aza-2-silacyclooctane (IX),
1854

REACTION OF PHENYLTRIFLUOROSILANE
Table 1. Quasisilatranes XI XIII and silatranes XIV and XV
1855
Found, %
Calculated, %
Comp.
no.
Yield,
%
mp,
C
Formula
C
H
F (Si)
N
C
H
F (Si)
N
XI
73
53
12
18
84
61
60 61
200
54.51
68.46
36.61
37.05
6.89
7.01
7.20
6.39
7.62
(9.38)
11.83
10.19
6.01
4.67
8.13
7.42
C H NO FSi 54.74
6.68
7.07
7.27
6.26
7.87
(9.51)
11.51
9.83
5.80
4.68
8.48
7.25
1
1
16
2
XII
XIII
XIV
C H NO Si
68.19
36.34
37.29
1
7
21
2
C H NO FSi
5 12 2
C H NO FSi
6
12
3
decomp.
XV
86
204 207 57.37
6.65
5.81
C H NO Si
57.35
6.77
5.57
1
2
17
3
O
2
HOCH CH2
F
F
F SiC H + (HOCH CH ) NH
NH
Si N H+ HF
(1)
3
6
5
2
2 2
C H
F SiOCH CH
3 2 2
6
6
I
IV
O
IX
H[F Si(OCH CH ) NH]
3
2
2 2
X
the first author as early as in 1958 (liquid 1,1-dime-
thylquasisilatrane and its N-ethyl derivative) [13]. It
seems that the transannular dative bond N Si in
these compounds is very weak if exists at all (at room
temperature) [14].
silane with methyl-bis(2-hydroxyethyl)amine (V) (2)
proceeds with rupture of two Si F bonds (rather than
C Si) and formation of intracomplex bicyclic 1-phe-
nyl-1-fluoro-5-methylquasisilatrane ((N Si) 2-phe-
nyl-2-fluoro-1,3-dioxa-6-aza-6-methyl-2-silacyclo-
octane) (XI) (Table 1).
Unlike reaction (1), reaction of phenyltrifluoro-
|
|
PhSiF + (HOCH CH ) NMe
FPhSi(OCH2CH2)2NMe + 2HF.
(2)
3
2
2 2
I
V
XI
Reaction of PhSiF (I) with methylbis(2-trimethyl-
siloxyethyl)amine (VI) proceeds as resilylation with
retention of the C Si bond, rupture of the Si F
bond, elimination of trimethylfluorosilane and forma-
tion of 1-phenyl-1-fluoro-5-methylquasisilatrane (XI)
(3).
3
PhSiF + (Me SiOCH CH ) NMe
FPhSi(OCH2CH2)2NMe + 2Me3SiF.
(3)
3
3
2
2 2
I
VI
XI
Reaction of diphenyldifluorosilane (II) with me-
thylbis(2-hydroxyethyl)amine (V) or methylbis(2-
trimethylsiloxyethyl)amine (VI) in molar ratio of 1:1
in both cases occurs with rupture of two Si F bonds
and leads to 1,1-diphenyl-5-methylquasisilatrane
silicon atom and transannular donor acceptor bond
N
Si (XII) (4).
Earlier the molecular structure of its analog, 1,1-
diphenylquasisilatrane (2,2-diphenyl-1,3-dioxa-6-aza-
2-silacyclooctane), was studied using the X-ray dif-
(
N
Si) 2,2-diphenyl-1,3-dioxa-6- aza-6-methyl-2-
silacyclooctane) (XII) containing pentacoordinate
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 12 2006

1856
VORONKOV et al.
Ph SiF + (ROCH CH ) NMe
Ph2Si(OCH2CH2)2NMe + 2RF.
XII
(4)
2
2
2
2 2
II
V, VI
R = H (V), Me Si (VI).
3
fraction pattern method to provide the evidence for its
trigonal-bipyramidal structure (interatomic distance
Methylphenyldifluorosilane (II) reacts with bis(2-
hydroxyethyl)amine (IV) to afford 1-methyl-1-fluoro-
quasisilatrane (XIII) (Table 1) (5).
N
Si is 2.301 ) [15].
MePhSiF + (HOCH CH ) NH
C H + MeFSi(OCH CH ) NH + HF.
6
6
2
2 2
(5)
2
2
2 2
II
IV
XIII
In the reaction of phenyltrifluorosilane I with tris-
2-hydroxyethyl)amine VII 1-fluorosilatrane XIV and
-phenylsilatrane XV are formed simultaneously in
molar ratio of 1:3 as a result of two parallel reactions,
alcoholysis of the two Si F bonds and protolysis of
the C Si bond (6), or alcoholysis of all three Si F
bonds (7).
silicon atom X, XI have been studied by us using
NMR spectroscopy for the first time.
(
1
The 29Si chemical shift in quasisilatranes IX XII is
shifted upfield as compared to compounds containing
tetrahedral silicon atom (F Si(OEt) , FPhSi(OEt) ,
2
2
2
Ph Si(OEt) and FMeSi(OEt) [9], Table 3) by 32, 19,
2
2
2
10, and 36 ppm, respectively. Its value decreases with
F SiC H + (HOCH CH ) N
3
6
5
2
2 3
the number of the Si F bonds in these molecules
XIII > X > XI > XII, that is indicative of the cor-
responding increase of the strength of transannular
bond N Si. Relatively small value of Si for quasi-
silatrane X is due to the fact that in its molecule (like
|
|
(
6)
C H + FSi(OCH CH ) N + 2HF,
6
6
2
2 3
XIV
|
|
PhSi(OCH CH ) N + 3HF.
(7)
in silatranes) the value of
apart from the coordination contribution N Si, by
variation of the total charge [19].
is strongly affected,
2
2 3
Si
XV
Melting points, IR and NMR spectra of the sila-
tranes XIV and XV derivatives correspond to the
published data [11, 12, 16 18].
q
15N chemical shifts of quasisilatranes IX and X are
somewhat shifted downfield (by 3 and 8 ppm, respec-
tively) as compared to the chemical shifts in the spec-
tra of the starting bis(2-hydroxyethyl)amine
The reaction of PhSiF (I) with tris(2-trimethyl-
3
siloxyethyl)amine (VI) in hexane during 20 30 min
affords the expected 1-phenylsilatrane (XV) in 86%
yield (8).
(
(
351.4 ppm) and methyl-bis(2-hydroxyethyl)amine
353.2 ppm) [14] under the same conditions.
PhSiF + (Me SiOCH CH ) N
Insignificant difference in the 15N chemical shifts
can be explained by small deshielding of the nitrogen
atom upon its protonation in alkyl amines [20] and
contribution of the cyclization effect [14].
3
3
2
2 2
I
VI
|
|
PhSi(OCH CH ) N + 3Me SiF.
(8)
2
2 2
3
XV
IR spectra of 1-fluorosilatrane XIV and 1-phenyl-
silatrane XV are identical to those published earlier
[10, 17]. The strong bands at 730 800 and 1080
1100 cm 1 in their IR spectra [11, 17] correspond to
backbone vibrations of the Si O C moieties. The
phenyl group in the spectrum of XV is represented by
The composition and the structure of the syn-
thesized quasisilatranes XI XIII and silatranes XIV
and XV was proved by elemental analysis (Table 1),
H, C, N, F, Si NMR spectroscopy (Table 2),
and IR spectroscopy.
1
13
15
19
29
1
the bands of stretching vibrations of CH (3060 cm ),
1
The occurrence of transannular interaction N Si
in the molecules of quasisilatranes R R Si(OCH2
CH ) RN (R = R = Me, Ph, PhMe, PhPr, etc.; R =
C=C (1600 cm ) and deformation vibrations of CH
1
bonds in monosubstituted benzenes (690, 710 cm ).
Strong bands at 780 and 800 cm 1 in the spectrum of
XIV are assigned to Si F stretching vibrations [21]
(in the same region the bands of stretching vibrations
(Si O) are also observed [18]).
2
2
H, Me, Et, Pr, CM , Ph;) was proved by NMR spec-
”
3
troscopy [14]. However, the so far unknown quasi-
silatranes bearing one or two fluorine atoms at the
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 12 2006

REACTION OF PHENYLTRIFLUOROSILANE
1857
Table 2. Parameters of H, 13C, 15N, 19F, and 29Si NMR spectra of quasisilatranes X XIII and silatranes XIV, XV (in
1
DMSO-d6)
H, ppm (J, Hz)
C, ppm
NCH2
Comp.
no.
Si,
ppm
F,
ppm
JSi F
Hz
,
N,
ppm
NR (SiR)
1.67
NCH2
OCH2
NR (SiR)
42.95
OCH2
IX
X
2.91
3.61
49.90
54.10
57.43
59.83
127.2
80.3
25 C)
78.3
(50 C)
44.0
117.4
208.2
214.3
(25 C)
221.4
348.1
345.6
(25 C)
346.8
2.74; 2.65 4.01; 3.95
= 12.4 JAB = 12.1
(
(
7
7.51;
.32)
J
(127.93;
128.96;
AB
3
J = 6.04
(50 C)
(50 C)
1
31.86)
XIa
XII
1.69
7.34;
2.65;
J = 4.8
4.05
42.28
(127.64;
128.63;
55.60
43.94
61.51
3
(
7
.65)
1
1
33.51;
38.49)
2.87; 2.54 3.69; 3.53
58.51
82.1
107.4
136.5
209.9
126.3
343.0
= 12.0 JAB = 10.3 (0.73; 2JCF
=
3
JCF =
(
0.06;
JHF
J
AB
3
=
3
45.5)
3.4
J = 5.6
6
.85)
3J
=
HNCH
5
.9
XIV
XVa
2.92
J = 5.9
3.68
3.92
50.29
51.22
56.69
100.2
83.7
348.4
352.4
3
3
JCF
.7
57.85
=
3
(7.24;
.34)
2.93
J = 5.9
(127.27;
128.21;
3
7
1
1
34.11;
43.50)
a
In CDCl .
3
In the IR spectra of quasisilatranes X XIII, intense
Table 3. Parameters of 19F and 29Si NMR spectra of
bands having several maxima in the ranges of 650
model compounds F2 nR Si(OEt) [9]
n
2
1
7
50 and 1040 1150 cm are similar to the bands of
antisymmetrical and symmetrical stretching vibrations
Si O C in the spectra of alkoxysilanes [22]. In the
IR spectra of quasisilatranes XI and XII, as in the
spectrum of 1-phenylsilatrane XV, the absorption
bands of the phenyl group are present. Stretching
vibrations of the Si F bands in the spectra of quasi-
silatranes XI and XIII containing coordination bond
R
n
Si, ppm
F, ppm
JSi F, Hz
Ph
Ph
Me
2
1
1
0
34.5
61.5
46.0
95.7
142.4
154.7
262.0
193.4
a
a 29
Si chemical shift was calculated by additive scheme.
N
8
Si are responsible for the bands at 780 and
1
80 cm .
1
-Phenyl-1-fluoro-5-methylquasisilatrane (XI).
a. To 8.9 g of methyl-bis(2-hydroxyethyl)amine in
EXPERIMENTAL
10 ml of benzene 12.17 g of phenyltrifluorosilane I
was added dropwise at 3 to 0 C. The reaction mix-
ture was stirred for 30 min. The precipitate formed
was filtered and crystallized from DMF. 12.6 g (73%)
of compound XI was obtained with mp 84 C.
IR spectra of the synthesized compounds were
registered on a Specord IR-75 spectrometer in pellets
1
13
15
19
29
with KBr. H, C, N, F, and Si NMR spectra
were recorded on a Bruker DÞX-400 spectrometer (at
4
00.13, 100.61, 40.56, 376.50 and 79.5 MHz, respec-
b. To 10.0 g of phenyltrifluorosilane I 16.24 g of
tively) in DMSO-d , internal standard TMS.
methyl-bis(2-trimethylsiloxyethyl)amine
IV
was
6
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 12 2006

1858
VORONKOV et al.
added dropwise during 1 h at room temperature. The
reaction mixture was stirred for 30 min. The precipi-
tate formed was filtered and crystallized from DMF.
REFERENCES
1. Voronkov, M.G., Trofimova, O.M., Chernov, N.F.,
Albanov, A.I., Chipanina, N.N., and Grebneva E.A.,
Appl. Organometal. Chem., 2005, vol. 19, no. 4,
p. 538.
14.88 g (40%) of compound XI was obtained with
mp 84 C.
1
,1-Diphenyl-5-methylquasisilatrane (XII). a. To
2
. Voronkov, M.G., Grebneva, E.A., Trofimova, O.M.,
Chernov, N.F., Albanov, A.I., and Chipanina, N.N.,
Dokl. Chem., 2006, vol. 409, no. 2, p. 139.
0
.86 g of methyl-bis(2-hydroxyethyl)amine in 10 ml
of benzene 1.6 g of diphenyldifluorosilane II were
added dropwise at 0 C. The reaction mixture was
stirred for 30 min. After vacuum distillation 1.14 g
3
. Voronkov, M.G., Trofimova, O.M., Grebneva, E.A.,
Bolgova, Yu.I., Albanov, A.I., Chipanina, N.N., and
Chernov N.F., Abstract of Papers, 14th International
Symposium on Organosilicon Chemistry, Wurzburg,
(
53%) of compound XII was obtained with mp 61 C.
b. To 3.61 g of diphenyldifluorosilane II in 10 ml
2
005, p. 199.
of hexane 4.32 g of methyl-bis(2-trimethylsiloxyethyl)-
amine at room temperature. The reaction mixture was
stirred for 30 min. The yield of compound XII for the
reversed order of mixing of the reagents was also 53%
4. Voronkov, M.G., Grebneva, E.A., Trofimova, O.M.,
Chernov, N.F., Albanov, A.I., and Chipanina, N.N.,
Abstarct of Papers, 7 Vserossiiskaya konferentsiya
Khimiya ftora (7th All-Russian Conf. Fluorine
Chemistry ), Moscow, 2006, p. 28.
(
2.54 g).
1
-Fluoro-1-methymetilkvazisilatran (XIII). To
5
. Grebneva, E.A., Trofimova, O.M., Chernov, N.F.,
Albanov, A.I., Chipanina, N.N., and Voronkov M.G.,
Absttract of Papers, Mezhdunarodnaya konferentsiya
Organicheskaya khimiya ot Butlerova i Beil’shteina
1
1.87 g of methylphenyldifluorosilane II 7.89 g of
bis(2-hydroxyethyl)amine IV in 10 ml of benzene
were added dropwise. The reaction mixture was
stirred for 30 min. After vacuum distillation 6.9 g
12%) of compound XIII was obtained with mp 60
1 C.
(
Int. Conf. Org. Chem. Organic Chemistry Since
Butlerov and Beilstein until Present ), St. Petersburg,
006, p. 495.
(
6
2
6
7
. Krebs, R., Schomburg, D., and Schutzler, R.,
Z. Naturforsch., 1985, vol. 40B, p. 282.
Reaction of phenyltrifluorosilane I with tris(2-
hydroxyethyl)amine (VII). To the solution of 6.08 g
of phenyltrifluorosilane I in 10 ml of p-xylene
. Voronkov, M.G., Chernov, N.F., and Perlova, E.M.,
Zh. Obshch. Khim., 1987, vol. 57, no. 1, p. 161.
5
.61 g of tris(2-hydroxyethyl)amine were added drop-
wise during 40 min at 5 to 0 C. The precipitate
formed was filtered and sublimed in vacuum. 5.8 g
8. Voronkov, M.G., Chernov, N.F., and Perlova, E.M.,
J. Organometal. Chem., 1988, vol. 341, nos. 1 3,
p. 225.
(
18%) of compound XIV was obtained. Simultaneously
.04 g (54%) of compound XV was isolated by
crystallization from p-xylene.
1
9
. Voronkov, M.G., Boyarkina, E.V., Gebel’, I.A., Al-
banov, A.I., and Basenko, S.V., Zh. Obshch. Khim.,
2
005, vol. 75, no. 12, 2018.
1
-Phenylsilatrane (XV). To 7.94 g of tris(2-tri-
methylsiloxyethyl)amine VI in 10 ml of hexane
.51 g of phenyltrifluorosilane I were added dropwise.
1
1
0. Voronkov, M.G., Grebneva, E.A., Trofimova, O.M.,
Albanov, A.I., Chernov, N.F., and Chipanina, N.N.,
Zh. Obshch. Khim., 2006, vol. 76, no. 12, p. 1938.
3
The reaction mixture was stirred for 10 min at 20 C.
The precipitate formed was filtered and crystallized
from hot p-xylene. 4.77 g (86%) of compound XV
was obtained with mp 204 207 C.
1. Pestunovich, V., Kirpichenko, S., and Voronkov, M.,
in: The Chemistry of Organic Silicon Compounds,
Rappoport, Z. and Apeloig, Y., Eds., New York: Wiley,
1
998, vol. 2, p. 1447.
2. Voronkov, M.G. and D’yakov, V.M., Silatrane
Silatrany), Novosibirsk: Nauka, 1978.
1
Parameters of NMR spectra for all synthesized
compounds are given in Table 2, and their IR spectra
are in the text.
(
13. Davydova, V.P., Voronkov, M.G., and Dolgov, B.N.,
in: Khimiya i prakticheskoe primenenie kremniiorga-
nicheskikh soedinenii. Trudy konf. Kremniiorgani-
cheskie monomery (Chemistry and Practical Use of
Organosilicon Compounds. Abstr. Conf. Organo-
silicon Monomers), Leningrad: CBTI, 1958, vol. 1,
p. 204.
ACKNOWLEDGMENTS
This work was supported by the Council on grants
of the President of Russian Federation (NSh-4575.
006.3) and INTAS (Grant No. 03-51-4164).
2
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 12 2006

REACTION OF PHENYLTRIFLUOROSILANE
1859
1
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1
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