Reaction of secondary phosphine chalcogenides with 2,2,2- trichloroacetaldehyde

Article abstract of DOI:10.1134/S1070363209100041

The nucleophilic addition of secondary phosphine chalcogenides to 2,2,2-trichloroacetaldehyde proceeds under mild noncatalytic conditions (12-25dgC, 15-90 min) with the formation of functional tertiary phosphine chalcogenides, containing hydroxy groups in

Full text of DOI:10.1134/S1070363209100041

ISSN 1070-3632, Russian Journal of General Chemistry, 2009, Vol. 79, No. 10, pp. 2102–2107. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © N.I. Ivanova, N.K. Gusarova, N.А. Konovalova, P.А. Volkov, G.G. Levkovskaya, L.I. Larina, B.А. Trofimov, 2009, published in
Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 10, pp. 1607–1612.
Reaction of Secondary Phosphine Chalcogenides
with 2,2,2-Trichloroacetaldehyde
N. I. Ivanova, N. K. Gusarova, N. А. Konovalova, P. А. Volkov,
G. G. Levkovskaya, L. I. Larina, and B. А. Trofimov
Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: n_iva@irioch.irk.ru
Received April 22, 2009
Abstract―The nucleophilic addition of secondary phosphine chalcogenides to 2,2,2-trichloroacetaldehyde
proceeds under mild noncatalytic conditions (12–25°С, 15–90 min) with the formation of functional tertiary
phosphine chalcogenides, containing hydroxy groups in up to 98% yield. Using the method of concurrent
reactions the reactivity of secondary phosphine chalcogenides in this reaction was shown to decrease in the
order: (PhCH2CH2)2P(O)H >> (PhCH2CH2)2P(S)H > (PhCH2CH2)2P(Sе)Н, and the secondary bis[2-(2-pyridyl)
ethyl]-phosphine oxide was more reactive than bis(2-phenethyl)phosphine oxide.
DOI: 10.1134/S1070363209100041
The chemistry of tertiary phosphine chalcogenides
is actively developing. These compounds are more and
more widely used as ligands for metal complex
catalysts [1–6], intermediates and special solvents for
preparation of semiconducting nanomaterials [7–10],
extragents for noble, rare-earth, and transuranium
elements [11–13], antipyrens for nonflammable poly-
mers [14–16], reagents for preparation of the corres-
ponding phosphines [17]. A special attention is paid to
functional tertiary phosphine chalcogenides (contain-
ing, for example, hydroxy groups [5, 6, 18–21] or halo-
gen atoms [4, 22–25]), used for the design of metal
complex catalysts of the phase-transfer reactions and reactive
synthons for organic and organoelemental synthesis.
phosphine chalcogenides with functional aldehydes, in
particular, with commercially available 2,2,2-trichloro-
acetaldehyde. Yet, the data on this reaction are limited.
The reaction of secondary phosphine oxides and
phosphine sulfides containing aryl or alkyl radicals
with 2,2,2-trichloroacetaldehyde proceeding in in the
presence of basic catalysts or under noncatalytic
conditions was briefly mentioned [26–30]. Recently, a
report appeared on the first example of preparation of
1-[bis(2-phenethyl)phosphoroselenoyl]-2,2,2-trichloro-
1-ethanol from 2,2,2-trichloroacetaldehyde and bis-(2-
phenethyl)phosphine selenide [36]. The latter belongs
to a rare type of secondary phosphine chalcogenides
containing in the molecule the alkylaryl fragments.
Such phosphine chalcogenides become nowadays
available since trhey are readily prepared from red
phosphorus (Pn) and styrenes or vinylpyridines [20, 21].
One of the most convenient approaches to synthesis
of these compounds is the reaction of secondary
(1) KOH/H2O
X
(RCH2CH2)2P(X)H,
(1)
Pn
(RCH2CH2)2PH
(2) RCH=CH2/KOH/DMSO
R = Ph, 4-tert-Bu-C6H4, 2-Py; X = O, S, Se.
The chemistry of bis[2-aryl(hetaryl)ethyl]phosphine
chalcogenides is now actively developed, first of all,
by the example of their addition to multiple carbon-
carbon [32–35] and C=O bonds [36–38]. In particular,
their reactions with aromatic and heteroaromatic
aldehydes were described [39–42]. However, there are
2102

REACTION OF SECONDARY PHOSPHINE CHALCOGENIDES
2103
no data in the literature on the relative reactivity of
secondary phosphine oxides, phosphine sulfides and
phosphine selenides in these processes.
convenient atom-economic method for the synthesis of
new polyfunctional tertiary phosphine chalcogenides
(IIIa–IIIf).
In the present work, we have for the first time
studied the relative reactivity of the aforementioned
PH-addends on the example of the reaction of bis(2-
phenethyl)-phosphine chalcogenides (IIa–IIc) and bis
[2-(2-pyridyl)ethyl]phosphine chalcogenides (IId–IIf)
with 2,2,2-trichloroacetaldehyde, and developed a
The experiments have shown that secondary
phosphine chalcogenides IIa–IIf react with 2,2,2-
trichloroacetaldehyde under mild conditions (12–25°C,
15–90 min, dioxane, THF or benzene, argon) to form
the corresponding tertiary hydroxy-containing phos-
phine chalcogenides IIIа–IIIf (see the table).
Y
Y
X
H
X
O
H
12−25oC
15−90 min
P
CCl3
OH
IIIа−IIIf
(2)
P
CCl3C
+
Y
Y
I
IIа−IIf
Preparative yield of compounds IIIа–IIId, IIIf
under these conditions was 89–98%. At the same time,
the yield of phosphine sulfide IIIe was only 59%. It
turned out that under the reaction conditions it is
oxidized to the corresponding tertiary phosphine oxide
IIId (31P NMR) (the table, run 7). It should be also
noted that the reaction of the secondary pyridyl-
phosphine selenide IIf with 2,2,2-trichloroacetalde-
hyde at room temperature in THF is followed by
formation of the side oxidation products of both the
starting and the formed phosphine selenides, that leads
to substantial decrease of the yield of the target
product IIIe (to 43%) (see the table, run 8). However,
the latter can be obtained in the preparative yield of
94% by performing the reaction at 12–13°C in benzene
(the table, run 9).
Reaction of secondary phosphine chalcogenides IIa–IIf with 2,2,2-trichloroacetaldehydea
Yield of III, %
Run
no.
Phosphine
Temperature,
°C
Time,
Solvent
(3 ml)
X
Y
Adduct III
b
c
chalcogenides (II)
мин
1
2
3
4
5
6
7
8
9
О
СН
СН
СН
СН
N
23–25
23–25
23–25
23–25
23–25
15–16
15–16
23–25
12–13
15
15
60
90
12
35
60
10
90
dioxane
THF
99
98
97
99
97
98
72d
74
99
97
96
92
89
93
94
59
43
94
а
а
b
c
d
d
e
f
а
а
b
c
d
d
e
f
О
S
dioxane
dioxane
THF
Se
O
O
S
N
benzene
benzene
THF
N
Se
Se
N
N
benzene
f
f
a
The experiments were carried out under gas (argon); in all runs 1 mmol of phosphine chalcogenide IIa–IIf and 1.1 mmol of
trichloroacetaldehyde were taken. Yields calculated from 31Р NMR spectra. Preparative yield. In the reaction mixture alongside
tertiary pyridyl ethylphosphine sulfide IIIe was identified by 31Р NMR spectrum also tertiary pyridylethylphosphine oxide IIId in a ratio
72:28 percent.
b
c
d
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

2104
IVANOVA et al.
31
As can be seen from the table, hydrophos-
phine chalcogenides IIa–IIc in the P NMR spectrum
(31.2, 21.3 and 2.7 ppm, respectively), as well as by
synchronous increase in the integral intensity of the
signals of the formed hydroxy phosphine chalco-
genides IIIa–IIIc (51.4, 59.9 and 53.1 ppm, respec-
tively).
phorylation of 2,2,2-trichloroacetaldehyde proceeds
faster with phosphine oxides IIa, IId, whereas the
completion of the reaction with phosphine selenides
IIa, IIf requires the longest time.
For more correct estimation of the relative
reactivity of the secondary phosphine chalcogenides in
this reaction we have studied concurrent reactions of
2,2,2-trichloroacetaldehyde with bis(2-phenethyl)
phosphine oxide IIa, phosphine sulfide IIb and
phosphine selenide IIc taken in the molar ratio of
3.3:1:1:1 by the method of 31P NMR spectroscopy. The
experiment was performed in the NMR tube at room
temperature. Secondary phosphine chalcogenides IIа–
IIc were used in the form of 1.25 M. solutions in THF.
The analysis of the obtained data (Fig. 1) shows
that the reactivity of the secondary phosphine
chalcogenides IIa–IIc in the reaction with 2,2,2-tri-
chloroacetaldehyde decreases in the order: phosphine
oxide IIa >> phosphine sulfide IIb > phosphine
selenide IIc.
This is clear from scheme (3), which suggests that
nucleophilic addition of the secondary phosphine
chalcogenides to aldehydes under noncatalytic condi-
tions occurs via the tautomeric form A with a three-
coordinate phosphorus atom.
The process was followed by the decrease in the
integral intensity of the signals of the starting phos-
O
CCl3C
H
H
P
HX
IIIа−IIIf
P
(3)
X
A
X = O, S, Se.
Formation of nucleophile A from the secondary
phosphine oxide is more favorable (that is, its
concentration is higher) than with the corresponding
phosphine sulfide and phosphine selenide [42].
For bis(2-phenethyl)phosphine oxide (IIa) and bis-
[2-(2-pyridyl)ethyl]phosphine oxide (IId) the relative
reactivity in the reaction with 2,2,2-trichloro-
acetaldehyde was evaluated by the same method in
benzene at room temperature with the molar ratio of
the reagents of 1:1:2.2.
IIIb
IIIа
100
90
80
70
60
50
40
30
20
10
0
IIIc
The process was followed by the decrease in the
integral intensity of the signals of the starting
phosphine chalcogenides IIa, IId in the 31P NMR
spectrum (27.5 and 30.6 ppm), as well as by
synchronous increase in the integral intensity of the
signals of the formed tertiary hydroxy phosphine
oxides IIIa, IIId (48.1 and 49.7 ppm, respectively).
The experiment has shown that compound IId is more
reactive; its conversion reached 74% as soon as after 6
min, whereas the same conversion of compound IIa
was achieved only after 35 min (Fig. 2). A higher
reactivity of IId as compared to IIa is apparently due
to the fact that the pyridyl moiety, as a base, favors
deprotonation of the substrate, thus increasing the rate
of the reaction.
IIc
IIb
IIа
0
20
Time, min
40
60
Fig. 1. Dynamics of formation of tertiary phosphine
chalcogenides IIIa–IIIc and conversion of secondary
phosphine chalcogenides IIa–IIc in the reaction with 2,2,2-
trichloroacetaldehyde (room temperature, THF).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

REACTION OF SECONDARY PHOSPHINE CHALCOGENIDES
2105
1
The most characteristic signals in the H NMR
100
90
spectra of the obtained compounds IIIa–IIIf are those
of the CH group in the ОCHP=Х fragment: the doublet
at 4.50 ppm with geminal coupling constants 31P–1H of
1–3 Hz for compounds IIIa, IIId, IIIf and the singlet
for compounds IIIb, IIIc, IIIe; in the 13C NMR
spectra the doublet at 78–81 ppm is characteristic with
1JPC = 72–75 Hz for phosphine oxides IIIa, IIId, 40–
58 Hz for phosphine sulfides IIIb, IIIe and 40–43 Hz
for phosphine selenides IIIc, IIIf. Nonequivalence of
the signals of two phenethyl or two pyridylethyl
groups at the phosphorus atom in the 1H and 13C NMR
spectra of phosphine chalcogenides IIIa–IIIf is due to
the presence of the chiral atom in the ОCHP=Х group.
IIIа
80
70
60
IIId
50
40
30
IId
20
10
0
IIа
0
20
40
30
Thus, we have for the first time studied the relative
reactivity of the secondary bis(2-phenethyl)phosphine
chalcogenides and bis[2-(2-pyridyl)ethyl]phosphine
chalcogenides in the reaction with 2,2,2-trichloro-
acetaldehyde and suggested a convenient atom-
economic method of synthesis of new polyfunctional
chiral tertiary α-hydroxy phosphine chalcogenides,
promising ligands for metal complex catalysis and
synthons for organic and organometallic synthesis.
Time, min
Fig. 2. Dynamics of formation of tertiary phosphine
chalcogenides IIIa, IIId and conversion of secondary
phosphine chalcogenides IIa, IId in the reaction with
2,2,2-trichloroacetaldehyde (room temperature, benzene).
1-[Bis(2-phenethyl)phosphoryl]-2,2,2-trichloro-
1-ethanol (IIIа) (see the table, run 1). Yield 0.39 g
(97%), mp 142–143°C (hexane). H NMR spectrum
EXPERIMENTAL
1
(CDCl3), δH, ppm: 2.27 m, 2.53 m (4H, PhCH2), 2.97
m, 3.11 m (4H, CH2P), 4.48 d (1H, PCH, 2JPH 3.6 Hz),
7.17–7.28 m (10H, Ph). 13C NMR spectrum (CDCl3),
δC, ppm: 27.51 (PhCH2), 27.65 (PhCH2), 29.04 d
IR spectra were taken on a Bruker IFS-25
1
13
spectrometer in thin layer and in KBr pellets. H, C,
and 31P NMR spectra were obtained on a Bruker DPX-
400 spectrometer (400, 101, and 162 MHz,
respectively), internal standard HMDS, external
standard 85% H3PО4 (31P). All experiments were
carried out in an inert atmosphere (argon).
1
1
(CH2P, JPC 61.0 Hz), 29.65 d (CH2P, JPC 61.0 Hz),
1
2
80.99 d (PCH, JPC 72.7 Hz), 98.96 d (CCl3, JPC
6.5 Hz), 126.66 (Cp), 128.12 (Co), 128.18 (Co), 128.80
3
3
(Cm), 140.32 d (Ci, JPC 13.3 Hz), 140.59 d (Ci, JPC
Synthesis of tertiary α-hydroxyphosphine chal-
cogenides (IIIa–IIIf) (general procedure). The
solution of phosphine chalcogenide IIa–IIf (1.0 mmol)
and 2,2,2-trichloroacetaldehyde (1.1 mmol) in 3 ml of
the solvent in an argon atmosphere was stirred at 12–
25°C for 10–90 min (see the table). The reaction was
monitored by 31P NMR spectroscopy by decrease of
intensity of the signals of the starting secondary
phosphine chalcogenides IIa–IIf in the range 2–
34 ppm and increase of intensity of the formed tertiary
phosphine chalcogenides IIIa–IIIf in the range 49–
60 ppm. The solvent was removed under reduced
pressure, the residue (for the products with the
phenethyl substituents) washed with ethanol (0.3 ml ×
3), dried at 1 mm Hg, to obtain products IIIa–IIIc (see
the table, runs 1–4); products IIId–IIIf after removal
of solvent were resedimented from chloroform into
hexane (see the table, runs 5–9).
31
13.3 Hz). P NMR spectrum (CDCl3), δP, ppm: 51.4.
IR (KBr, cm–1): 1149 ν (P=O); 1090 δ (COH); 819,
807 ν (CCl3). Found, %: C 53.36; H 5.06; P 7.59; Cl
25.96. C18H20Cl3О2P. Calculated, %: C 53.27; H 4.93;
P 7.64; Cl 26.26.
1-[Bis(2-phenethyl)phosphorothioyl]-2,2,2-tri-
chloro-1-ethanol (IIIb) (see the table, run 3). Yield
1
0.39 g (92%), mp 105–106°C (hexane). H NMR
spectrum (CDCl3), δH, ppm: 2.30 m, 2.50 m, 2.65 m,
2.95 m, 3.18 m (8H, PhCH2, CH2P), 4.28 s (1H, PCH),
7.17–7.29 m (10H, Ph). 13C NMR spectrum (CDCl3),
δC, ppm: 28.27 (PhCH2), 29.21 (PhCH2), 31.58 d
1
1
(CH2P, JPC 41.4 Hz), 33.87 d (CH2P, JPC 41.4 Hz),
1
78.33 d (PCH, JPC 40.0 Hz), 99.82 (CCl3), 126.49
(Cр), 127.87 (Cо), 127.96 (Cо), 128.52 (Cm), 139.45 d
3
3
(Ci, JPC 14.0 Hz), 139.71 d (Ci, JPC 14.2 Hz). 31P
NMR spectrum (CDCl3), δP, ppm: 59.9. IR (KBr, cm–1):
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

2106
IVANOVA et al.
1074 δ (COH); 817, 798 ν (CCl3); 592 ν (P=S). Found,
%: C 51.46; H 4.71; P 7.06; Cl 24.83; S 7.64.
C18H20Cl3ОPS. Calculated, %: C 51.26; H 4.78; P
7.34; Cl 25.22; S 7.61.
spectrum (CDCl3), δP, ppm: 60.0. IR (KBr, cm–1):
1052, 1076 δ (COH); 832, 802 ν (CCl3); 573 ν (P=S).
Found, %: C 45.63; H 4.39; P 7.28; Cl 24.99; N 6.58;
S 7.49. C16H18Cl3ОPN2S. Calculated, %: C 45.35; H
4.28; P 7.31; Cl 25.10; N 6.61; S 7.57.
1-[Bis(2-phenethyl)phosphoroselenoyl]-2,2,2-tri-
chloro-1-ethanol (IIIc) (see the table, run 4). Yield
0.42 g (89%), mp 89–90°C (hexane). 1H NMR
spectrum (CDCl3), δH, ppm: 2.43 m, 2.63 m (4H,
PhCH2), 2.76 m, 2.96 m (4H, CH2P), 4.26 d (1H, PCH,
2JPH 2.3 Hz), 7.17–7.28 m (10H, Ph). 13C NMR
spectrum (CDCl3), δC, ppm: 29.57 (PhCH2), 30.57
1-{Bis[2-(2-pyridyl)ethyl]phosphoroselenoyl}-
2,2,2-trichloro-1-ethanol (IIIf) (see the table, run 8).
0.3 g of the reaction mixture was obtained, which
contained, according to 31P NMR data, 74% of tertiary
phosphine selenide IIIf along with other phosphorus-
containing products, showing the following signals in
1
31
(PhCH2), 31.46 d (CH2P, JPC 37.0 Hz), 33.71 d
the P NMR spectrum (δP, ppm): 22.90, 41.36, 47.45,
1
1
(CH2P, JPC 39.0 Hz), 79.72 d (PCH, JPC 43.6 Hz)
(acetone-d6), 98.32 (CCl3), 126.84 (Cр), 128.25 (Cо),
49.73, 84.52. The reaction mixture was washed with
small portions of hexane, evacuated, and resedimented
from chloroform to hexane to obtain 0.20 g (43%) of
phosphine selenide IIIf as a light beige powder, mp
3
128.32 (Cо), 128.84 (Cm), 139.68 d (Ci, JPC 15.0 Hz),
139.95 d (Ci, JPC 15.0 Hz). 31P NMR spectrum
3
(CDCl3), δP, ppm: 53.1. IR (KBr, cm–1): 1065 δ
(COH); 817, 796 ν (CCl3); 481, 455 ν (P=Sе). Found,
%: C 46.23; H 4.41; P 6.65; Cl 22.29; Sе 17.12.
C18H20Cl3ОPSе. Calculated, %: C 46.13; H 4.30; P
6.61; Cl 22.69; Sе 16.86.
1
102–104°C (hexane) (decomp.). H NMR spectrum
(CDCl3), δH, ppm: 2.52 m, 2.65–2.72 m, 2.92 m (4H,
CH2P), 3.08–3.17 m, 3.38 m (4H, PуCH2), 4.50 (1H,
PCH), 7.12–7.32 m (H5, H3), 7.52–7.64 m (H4), 8.51 m
(H6). 13C NMR spectrum (CDCl3), δC, ppm: 28.56 d
1
1
(CH2P, JPC 41.8 Hz), 28.94 d (CH2P, JPC 40.9 Hz),
1-{Bis[2-(2-pyridyl)ethyl]phosphoryl}-2,2,2-tri-
1
31.44 (PyCH2), 81.52 d (PCH, JPC 39.9 Hz), 99.03
chloro-1-ethanol (IIId) (see the table, run 5). Yield
(CCl3), 121.93, 122.19 (C5, Py), 123.46, 123.95 (C3,
Py), 137.20, 137.76 (C4, Py), 148.43, 148.95 (C6, Py),
159.29 d (3JPC 13.6 Hz, C2, Py), 159.39 d (3JPC 13.6 Hz,
C2, Pу). 31P NMR spectrum (CDCl3), δP, ppm: 52.6. IR
(KBr, cm–1): 1052, 1076 δ (COH); 823, 800 ν (CCl3);
484 ν (P=Se). Found, %: C 40.97; H 3.82; P 6.86; Cl
22.02; N 5.88; Sе 16.33. C16H18Cl3ОPN2Se. Cal-
culated, %: C 40.83; H 3.86; P 6.58; Cl 22.60; N 5.95;
Sе 16.78.
1
0.38 g (93%), mp 118–119°C (hexane). H NMR
spectrum (DMSO-d6), δH, ppm: 2.13 m, 2.38 m (4H,
PуCH2), 2.98, 3.04 m (4H, CH2P), 4.80 d (1H, PCH,
2JPH 1.4), 8.48 m (H6), 7.71 m (H4), 7.29 m (H3), 7.19
m (H5). 13C NMR spectrum (DMSO-d6), δC, ppm:
1
1
25.11 d (CH2P, JPC 65.5 Hz), 27.62 d (CH2P, JPC
65.5 Hz), 29.11 (PyCH2), 29.39 (PyCH2), 79.56 d
1
(PCH, JPC 75.0 Hz), 94.99 (CCl3), 122.51 (C5, Py),
122.74 (C3, Py), 136.64 (C4, Py), 148.93 (C6, Py),
160.24 d (C2, Py, 3JPC 13.8 Hz), 160.47 d (3JPC 13.8 Hz,
C2, Py). 31P NMR spectrum (DMSO-d6), δP, ppm: 51.6.
IR (KBr, cm–1): 1065 δ (COH); 817, 796 ν (CCl3);
1157 ν (P=O). Found, %: C 46.99; H 4.39; P 7.38; Cl
26.11; N 6.84. C16H18Cl3О2PN2. Calculated, %: C
47.14; H 4.45; P 7.60; Cl 26.09; N 6.87.
ACKNOWLEDGMENTS
This work was performed with a financial support
from the Russian Foundation for Basic Research (grant
no. 07-03-00562).
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1-{Bis[2-(2-pyridyl)ethyl]phosphorothioyl}-2,2,2-
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13
7.47 m (H3, H5), 7.86 m (H4), 8.51 m (H6). C NMR
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