One-pot vinylation of secondary phosphine chalcogenides with vinyl sulfoxides

Article abstract of DOI:10.1080/10426500903329245

A facile, one-pot vinylation of secondary phosphine chalcogenides with alkyl(or aryl) vinyl sulfoxides has been elaborated. The vinylation comprises the nucleophilic addition of secondary phosphine chalcogenides to the vinyl sulfoxides (50 mol% KOH, dioxa

Full text of DOI:10.1080/10426500903329245

This article was downloaded by: [Florida State University]
On: 25 March 2013, At: 09:13
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered
office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Phosphorus, Sulfur, and Silicon and the
Related Elements
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/gpss20
One-Pot Vinylation of Secondary
Phosphine Chalcogenides with Vinyl
Sulfoxides
a
a
Svetlana F. Malysheva , Nina K. Gusarova , Natal'ya A. Belogorlova
a
a
a
a
,
Tamara V. Kashik , Leonid B. Krivdin , Sergei V. Fedorov
&
a
Boris A. Trofimov
a
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the
Russian Academy of Sciences, Irkutsk, Russia
Version of record first published: 25 Aug 2010.
To cite this article: Svetlana F. Malysheva , Nina K. Gusarova , Natal'ya A. Belogorlova , Tamara
V. Kashik , Leonid B. Krivdin , Sergei V. Fedorov & Boris A. Trofimov (2010): One-Pot Vinylation of
Secondary Phosphine Chalcogenides with Vinyl Sulfoxides, Phosphorus, Sulfur, and Silicon and the
Related Elements, 185:9, 1838-1844
To link to this article: http://dx.doi.org/10.1080/10426500903329245
PLEASE SCROLL DOWN FOR ARTICLE
Full terms and conditions of use: http://www.tandfonline.com/page/terms-and-conditions
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,
systematic supply, or distribution in any form to anyone is expressly forbidden.
The publisher does not give any warranty express or implied or make any representation
that the contents will be complete or accurate or up to date. The accuracy of any
instructions, formulae, and drug doses should be independently verified with primary
sources. The publisher shall not be liable for any loss, actions, claims, proceedings,
demand, or costs or damages whatsoever or howsoever caused arising directly or
indirectly in connection with or arising out of the use of this material.

Phosphorus, Sulfur, and Silicon, 185:1838–1844, 2010
Copyright ꢀ
Taylor & Francis Group, LLC
C
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500903329245
ONE-POT VINYLATION OF SECONDARY PHOSPHINE
CHALCOGENIDES WITH VINYL SULFOXIDES
Svetlana F. Malysheva, Nina K. Gusarova,
Natal’ya A. Belogorlova, Tamara V. Kashik, Leonid B. Krivdin,
Sergei V. Fedorov, and Boris A. Trofimov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian
Academy of Sciences, Irkutsk, Russia
A facile, one-pot vinylation of secondary phosphine chalcogenides with alkyl(or aryl) vinyl
sulfoxides has been elaborated. The vinylation comprises the nucleophilic addition of sec-
◦
ondary phosphine chalcogenides to the vinyl sulfoxides (∼50 mol% KOH, dioxane, 25–40 C,
1
h) followed by the elimination of sulfenic acids from the adducts (additional equivalent
◦
of KOH, 60–70 C, 1.5–2.0 h), the yields of target tertiary vinyl phosphine chalcogenides
reaching 92%.
Keywords Secondary phosphine chalcogenides; tertiary vinyl phosphine chalconedes; vinyl
sulfoxides; vinylation
INTRODUCTION
Vinyl phosphine chalcogenides are highly reactive building blocks that readily add
1
2
1e
3
4
various nucleophiles (amines, phosphines, thiols, carbanions ) and other reagents to
afford functionalized phosphine chalcogenides. The latter are widely applied as ligands for
5
6
the design of advanced catalysts, flame retardants, extractants of rare earth, transuranic and
noble elements, and coordinating solvents for the synthesis of conductive nanomaterials.
7
8
9
Conventional syntheses of vinyl phosphine chalcogenides employ toxic and haz-
ardous phosphorus halides and organometallics under inert an atmosphere, and are
laborious and do not meet modern ecological requirements. In the example of tert-
butylphenylphosphine oxide and 4-methylphenyl vinyl sulfoxide, the synthesis of tert-
butylphenylvinylphosphine oxide was briefly noted. However, experimental details as
well as proofs of the structure of the vinylphosphine oxide formed are not given in this
1
0
10
11
communication. The synthesis of two tertiary bis(arylalkyl)vinylphoshine oxides in low
19–34%) yields by the elimination of sulfenic acids from the adducts of secondary phos-
(
phine oxides to alkyl vinyl sulfoxides has also been reported. Consequently, this version
Received 25 June 2009; accepted 3 September 2009.
Financial support from the Russian Foundation for Basic Research (grants no. 07-03-00562 and 08-03-
0
0021) is gratefully acknowledged.
Address correspondence to Boris A. Trofimov, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian
Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033, Irkutsk, Russia. E-mail: boris trofimov@
irioch.irk.ru
1
838

VINYLATION OF SECONDARY PHOSPHINE CHALCOGENIDES
1839
of reaction could not be considered as synthetically useful. Meanwhile, in principal, such
an approach, when further properly elaborated up to a high-yield version and extended
to phosphine sulfides and phosphine selenides as well as to aryl vinyl sulfoxides, could
become general efficient synthesis of vinylphosphine chalcogenides.
To reach this goal, in this work we have thoroughly studied the nucleophilic addition of
secondary phosphine chalcogenides to organyl vinyl sulfoxides followed by the elimination
of sulfenic acids from the intermediary adducts without their isolation. Eventually, our
efforts led to elaboration of the one-pot synthesis of tertiary vinyl phosphine chalcogenides,
mostly in high preparative yield.
RESULTS AND DISCUSSION
As representativesecondaryphosphinechalcogenides, bis[2-(phenyl)ethyl]phosphine
oxide (1), bis[2-(phenyl)ethyl]phosphine sulfide (2), and bis[2-(phenyl)ethyl]phosphine
12
selenide (3), directly prepared from red phosphorus and styrene have been chosen
Scheme 1).
(
X
H
KOH/H O
X
2
Pn
[PH /H ]
P
H
P
3
2
PhMe
KOH/DMSO
X = O (1), S (2), Se (3)
1-3
Scheme 1
It was found that phosphine chalcogenides 1–3 added to ethyl vinyl sulfoxide (4)
or phenyl vinyl sulfoxide (5) under mild conditions (∼0.5 equivalent of KOH, dioxane,
◦
2
5–40 C, 1 h) to give regioselectively adducts 6–9 (Stage 1). The latter, without isolation,
◦
have been further heated (60–70 C, 1.5–2.0 h) in the presence of an additional amount (∼1
equivalent) of KOH (Stage 2) to afford the target vinylphosphine chalcogenides 10–12 in
87%, 92%, and 30% yields, respectively (Scheme 2).
The decreased yield of vinyl phosphine selenide 12 is due to selenium extrusion from
starting 3, intermediary 8, and final 12 products. Elemental selenium thus precipitated reacts
with secondary phosphine selenide 3 and KOH to furnish the potassium salt of phosphinic
31
13
acid 13 (identified by P NMR technique using external standard ), as shown in Scheme 3.
The vinylation of secondary phosphine chalcogenides 1–3 involves their addition to
organyl vinyl sulfoxides 4, 5, and elimination of organyl sulphenic acids from the adducts
6
–9. The sulfenic acids in the presence of KOH are transformed to salts 14 and 15 (Scheme
4).
Salt 14 was isolated in the mixture with KOH. The data of potentiometric acidimetric
titration have shown that the content of salt 14 in the mixture reaches 92%.
The excess KOH (∼1.5 equivalent) in this vinylation is crucial to tie up the released
sulfenic acids, which, otherwise, could add back to the active double bond of vinylphosphine
chalcogenides 10–12 to restore the adducts 6–9. Indeed, with ∼0.5 equivalent of KOH,
both the conversion of the adducts 6–9 and the yields of vinylated phosphine chalconedes
31
1
0–12 drop significantly ( P NMR monitoring).

1
840
S. F. MALYSHEVA ET AL.
R
H
X
KOH/Dioxane
Ar
P
S
O
1-3
4, 5
O
S
R
KOH/Dioxane
RSOH
P
P
X
X
6-9
1
0-12
R = Et, X = O (1, 4, 6, 10); R = Et, X = S (2, 4, 7, 11); R = Et, X = Se (3, 4, 8, 12); R = Ph,
X = S (2, 5, 9, 11)
Scheme 2
Se
Se
K+
P
+
Se + KOH
P
H
Se
3
13
Scheme 3
KOH/Dioxane
6
-9
10-12
RSOK
4,15
o
6
0-70 C, 1.5-2 h
1
R = Et (14); Ph (15)
Scheme 4
The previously unknown vinylphosphine chalcogenides 11 and 12 which are now
available prove to be convenient precursors of the novel vinylphosphine 16. Thus, the
◦
reduction of vinyl sulfide 11 and vinyl selenide 12 with sodium metal in toluene (100 C,
4
h) proceeds smoothly and almost quantitatively (Scheme 5).
Na/PhMe
1
1 or 12
P
o
1
00 C, 4 h
1
6
Scheme 5
Surprisingly, vinylphosphine oxide 10, under the same conditions, was found to be
practically inert (the conversion was near to zero). In this case, the conventional proto-
14
col for the phosphine oxide reduction with SiHCl3 also failed; a complex mixture of

VINYLATION OF SECONDARY PHOSPHINE CHALCOGENIDES
1841
various products containing neither initial vinylphosphine oxide 10, nor the expected vinyl
phosphine 16, was formed.
In conclusion, in the examples of ethyl vinyl and phenyl vinyl sulfoxides, it has
been shown that organyl vinyl sulfoxides are convenient and effective vinyl synthons for
the secondary phosphine oxides, phosphine sulfides, and phosphine selenides and allow
for preparation of hitherto unknown or scarcely available tertiary vinylphosphine chalco-
genides. The latter are recognized to be reactive building blocks for organic synthesis and
convenient models for physicochemical studies, e.g., for conformational analysis and stere-
ochemical dependences of 31P– H spin–spin coupling constants of di(2-phenethyl)vinyl
1
15
phosphine and related phosphine chalcogenide.
EXPERIMENTAL
IR spectra were measured with a Bruker IFS 25 instrument in microlayers or KBr
cm ). H, C, and P NMR spectra were recorded on a Bruker DPX-400 spectrometer
400.13, 100.61, and 161.98 MHz, respectively) in CDCl3 solutions and referenced to
−1
1
13
31
(
(
1
13
31
internal HMDS ( H), CHCl3 ( C), and external 85% H3PO4 ( P). Two-dimensional homo-
and heteronuclear NMR correlation experiments (NOESY, HSQC) were used to assign the
1
13
31
signals in H and C NMR spectra. The reaction was monitored by P NMR (decrease of
signals in the region of 3–33 ppm for phosphine chalcogenides 1–3 and increase of signals
at 33–43 ppm for vinyl phosphine chalcogenides 10–12). Potentiometric titration in water
◦
was performed on an EV-74 instrument at 20 C using glass chlorosilver electrodes filled
with aqueous solution of LiCl and AgCl salts, with 0.1 N aqueous solution of HCl being a
titrant. The concentration of the salt studied ranged 5–10 mmol. The concentration basicity
6
constant of the salt studied was determined by potentiometry in water using imidazole as
a standard.
Synthesis of Tertiary Phosphine Oxide 10
A mixture of phosphine oxide 1 (1.4 mmol), sulfoxide 4 (1.4 mmol), and powdered
KOH·0.5H2O (0.7 mmol) in dioxane (10 mL) was stirred at ambient temperature for 1 h
and analyzed by 31P NMR. In the spectrum, a signal of initial phosphine oxide 1 at 28.07
31
ppm disappeared, and a signal at 47.89 ppm attributable to the adduct 6 was observed ( P
10
NMR using external standard ). To the reaction mixture, KOH·0.5H2O (1.4 mmol) was
◦
31
also added, and the suspension was stirred at 60 C for 2 h. In the P NMR spectrum,
a signal at 36.62 ppm assigned to vinyl phosphine oxide 10 was detected. The reaction
mixture was cooled, the residue was filtered off, dioxane was removed, and the product
obtained was dried under lowered pressure to give 0.35 g (87%) of vinyl phosphine oxide
10 (purified by recrystallization from acetone).
Bis(2-phenethyl)vinylphosphine Oxide (10)
◦
1
Colorless crystals, 0.35 g (87%) yield, mp 92 C (acetone). H NMR, δ (ppm), J
(
Hz): 1.99–2.11 (m, 4H, CH2P), 2.86–2.94 (m, 4H, CH2Ph), {6.14 [1H, H(3)], 6.25 [1H,
2 3 3 2
H(1)], 6.38 [1H, H(2)], JH(1)H(2) = 1.4, JH(1)H(3) = 12.6, JH(2)H(3) = 18.5, JPH(3) =
3
3
13
2
2
1
8.0, JPH(1) = 37.9, JPH(2) = 20.8}, 7.18–7.28 (m,10H, Ph). C NMR, δ (ppm), J (Hz):
2
1
7.60 (d, JPC 3.0, CH2Ph), 31.60 (d, JPC 67.0, PCH2CH2Ph), 126.50 (C-p), 128.10 (C-o),
1
3
28.70 (C-m), 130.70 (d, JPC = 86.8, CH2), 135.20 ( CH), 141.0 (d, JPC = 14.1,

1
842
S. F. MALYSHEVA ET AL.
C-i). 31P NMR, δ (ppm): 36.0. IR (KBr), ν, cm : 1603 (C Cvinyl); 1167 (P O). Anal.
−1
Calcd. for C18H21OP: C, 75.35; H, 7.24; P, 9.93. Found: C, 76.04; H, 7.44; P, 10.89.
Synthesis of Tertiary Phosphine Sulfide 11
A mixture of phosphine sulfide 2 (2.2 mmol), sulfoxide 4 (2.2 mmol), and powdered
◦
KOH·0.5H2O (1.1 mmol) in dioxane (10 mL) was stirred at 25 C for 1 h. In the spectrum,
a signal of initial phosphine sulfide 2 at 22.24 ppm disappeared, and a signal at 48.92
3
1
12a
ppm assigned to the adduct 7 was observed ( P NMR using external standard ). To the
reaction mixture, KOH·0.5H2O (0.12 g, 2.2 mmol) was added, and the resulting mixture
◦
31
was then heated at 70 C for 1.5 h. In the P NMR spectrum, a signal at 42.21 ppm assigned
to vinyl phosphine oxide 11 was detected. Next, the precipitate was filtered off, the solvent
was removed, the reside was dried in vacuum, and the product obtained was reprecipitated
from diethyl ether to hexane to afford 0.60 g (yield 91%) of vinyl phosphine sulfide 11.
The residue was subsequently washed with dioxane and ether, dried in vacuum to
give 0.17 g of the product.
The product obtained was analyzed by potentiometric acidimetric titration in aqueous
solution. The titration curve shows two jumps, the first one corresponding to the neutral-
ization of excess KOH, the second one relating to the neutralization of potassium salt of
ethanesulfenic acid 14. The basicity of potassium ethanesulfenate (14) (the value of the acid
dissociation constant pKa = 6.18) is significantly weaker than that of potassium hydroxide
totally ionized in water. According to the potentiometric titration data, the product contains
92% of this salt.
Vinyl phosphine sulfide 11 was synthesized in 92% yield from secondary phosphine
sulfide 2 and phenyl vinyl sulfoxide 5 under the same conditions.
Bis(2-phenethyl)vinylphosphine Sulfide (11)
1
Viscous, paraffin-like, light-yellowish product, 0.60 g (91%). H NMR, δ (ppm), J
Hz): 2.13–2.28 (m, 4H, CH2P), 2.79–3.06 (m, 4H, CH2Ph), {6.22 [1H, H(3)], 6.25 [1H,
(
2
3
3
2
H(1)], 6.47 [1H, H(2)], JH(1)H(2) = 1.6, JH(1)H(3) = 11.5, JH(2)H(3) = 17.6, JPH(3) = 26.8,
3
3
13
JPH(1) = 44.0, JPH(2) = 24.4}, 7.20–7.33 (m, 10H, Ph). C NMR, δ (ppm), J (Hz): 28.30
d, JPC = 2.1, CH2Ph), 34.20 (d, JPC = 52.8, CH2P), 126.50 (C-p), 128.30 (C-o), 128.70
2
1
(
(
1
2
3
C-m), 130.10 (d, JPC = 69.9, CH2 ), 135.20 (d, JPC = 1.1, CH), 140.8 (d, JPC = 15.1,
31
−1
C-i). P NMR, δ (ppm): 42.52. IR, ν, cm : 1602 (C Cvinyl); 543 (P S). Anal. Calcd.
for C18H21PS: C, 71.82; H, 6.99; P, 10.91; S, 10.51. Found: C, 71.97; H, 7.05; P, 10.31; S
10.67.
Synthesis of Tertiary Phosphine Selenide 12
A mixture of 0.64 g phosphine selenides 3 (0.21 g, 2.0 mmol), sulfoxide 4 (2.0 mmol),
◦
and ground KOH (0.06 g, 1.0 mmol) in dioxane (10 mL) was stirred at 40 C for 1 h. In
the spectrum, a signal of initial phosphine selenide 3 at 2.99 ppm disappeared, and the
signals at 36.49 ppm assigned tentatively to phoshine selenide 8, 33.36 ppm related to
vinyl phosphine oxide 12, and 24.70 ppm corresponding to potassium salt of phosphinic
3
1
13
acid were observed ( P NMR using external standard ). To the reaction mixture, KOH
◦
31
(
0.11 g, 2.0 mmol) was added, and the mixture was heated at 70 C for 1.5 h. The
P
NMR spectrum showed the signals at 33.36 ppm assigned to vinyl phosphine oxide 12 and

VINYLATION OF SECONDARY PHOSPHINE CHALCOGENIDES
1843
24.70 ppm assigned to potassium salt of phosphinic acid. The reaction mixture was cooled,
diethyl ether (5 mL) was added, the suspension obtained was filtered off, the solvent was
removed, the product was dissolved in chloroform and reprecipitated in hexane, and the
latter was removed to give 0.21 g (yield 30%) of phosphine selenide 12.
The residue was consequently washed with chloroform, dioxane, and water and dried
in air to give 0.01 g of elemental selenium.
Bis(2-phenethyl)vinylphosphine Selenide (12)
1
Light-yellowish oil. H NMR, δ (ppm), J (Hz): 2.22–2.31 (m, 4H, CH2P), 2.71–3.06
2
3
(
1
m, 4H, CH2Ph, {6.21 [1H, H(3)], 6.25 [1H, H(1)], 6.47 [1H, H(2)], JH(1)H(2) 2.2, JH(1)H(3)
3
3
3
3
13
1.6, JH(2)H(3) 17.6, JPH(3) 24.6, JPH(1) 45.4, JPH(2) 24.6}, 7.17–7.26 (m, 10H, Ph).
C
2
1
NMR, δ (ppm), J (Hz): 29.10 (d, JPC = 2.2, CH2Ph), 33.91 (d, JPC = 45.4, CH2P), 126.60
1
2
(
C-p), 128.30 (C-o), 128.70 (C-m), 128.80 (d, JPC = 75.4, CH2), 137.60 (d, JPC = 2.2,
3 31 77
CH), 140.6 (d, JPC = 15.3, C-i). P NMR, δ (ppm): 33.26. Se NMR (76.31 MHz,
1
−1
CDCl3): δ = −433.0 (d, JPSe = 716.1 Hz). IR, ν, cm : 1602 (C Cvinyl); 448 (P Se).
Anal. Calcd. for C18H21PSe: C, 61.82; H, 6.13; P, 9.01; Se, 22.51. Found: C, 62.25; H,
6.09; P, 8.92; S 22.74.
Synthesis of Tertiary Phosphine 16
The suspension of phosphine sulfide 11 (1.5 mmol) or phosphine selenide (1.5 mmol)
◦
1
2 and sodium (4.5 mmol) in toluene (5 mL) was vigorously stirred at 100 C for 4 h. In the
3
1
P NMR spectrum, the signals at 41.21 ppm assigned to phosphine sulfide 11 or 33.09 ppm
assigned to phosphine selenide 12 disappeared, and a signal at −26.37 ppm corresponding
to phosphine 16 appeared. The reaction mixture was cooled, filtered off, and toluene was
removed to afford phosphine 16.
Bis(2-phenethyl)vinylphosphine (16)
1
Light-yellowish oil, 0.4 g (yield 90%). H NMR, δ (ppm), J (Hz): 1.67–1.71 (m, 4H,
CH2P), 2.68–2.74 (m, 4H, CH2Ph), {6.14 [1H, H(1)], 6.18 [1H, H(2)], 6.58 [1H, H(1),
2
3
3
3
3
H(3), JH(1)H(2) = 2.2, JH(1)H(3) = 11.7, JH(2)H(3) = 18.4, JPH(3) = 5.8, JPH(1) = 30.4,
3
13
2
JPH(2) = 13.17}, 7.11–7.25 (m, 10H, Ph). C NMR, δ (ppm), J (Hz): 32.56 (d, JPC = 14.0,
1
CH2Ph), 29.73 (d, JPC 13.2, CH2P), 126.02 (C-p), 127.80 (C-o), 128.40 (C-m), 140.0 (d,
1
2
3
31
JPC = 19.6, CH2 ), 128.10 (d, JPC = 19.6, CH ), 143.11 (d, JPC 10.0 C-i). P NMR,
δ (ppm): −26.80. IR, ν, cm : 1603 (C Cvinyl). Anal. Calcd. for C18H21P: C, 80.82; H,
.99; P, 11.21. Found: C, 80.57; H, 7.89; P, 11.54.
−1
7
REFERENCES
1
. (a) A. M. Maj, K. M. Pietrusiewicz, I. Suisse, F. Agbossou, and A. J. Mortreux, J. Organomet.
Chem., 626, 157 (2001); (b) M. S. Rahman, M. Oliana, and K. K. Hii, Tetrahedron: Asymmetry,
15, 1835 (2004); (c) D. V. Griffiths, H. J. Groombridge, P. M. Mahoney, S. P. Swetnam, G.
Walton, and D. C. York, Tetrahedron, 61, 4595 (2005).
2. (a) P. Barbaro, C. Bianchini, G. Giambastiani, and A. Togni, Chem. Commun., 22, 2672 (2002);
(
(
b) M. Alajarin, C. Lopez-Leonardo, and P. Llamas-Lorente, Lett. Org. Chem., 1, 145 (2004);
c) L.-B. Han and C.-Q. Zhao, J. Org. Chem., 70, 10121 (2005).

1
844
S. F. MALYSHEVA ET AL.
3. (a) K. M. Pietrusiewicz and M. Zablocka, Tetrahedron Lett., 29, 937 (1988); (b) R. T. Paine, E.
M. Bond, S. Parveen, N. Donhart, E. N. Duesler, K. A. Smith, and H. Noth, Inorg. Chem., 41,
4
44 (2002).
4
. (a) K. M. Pietrusiewicz, W. Holody, M. Koprowski, S. Cicchi, A. Goti, and A. Brandi, Phos-
phorus, Sulfur, and Silicon, 144–146, 389 (1999); (b) A. R. Katritzky, M. Piffl, H. Lang, and E.
Anders, Chem. Rev., 99, 665 (1999); (c) K.-W. Tan, F. Liu, Y. Li, G.-K. Tan, and P.-H. Leung,
J. Organomet. Chem., 691, 4753 (2006).
5
6
7
. (a) Q. Dai, W. Gao, D. Liu, L. M. Kapes, and X. J. Zhang, Org. Chem., 71, 3928 (2006); (b) D.
Benito-Garagorri, J. Wiedermann, M. Pollak, K. Mereiter, and K. Kirchner, Organometallics,
2
6, 217 (2007).
. (a) G. Ribera, L. A. Mercado, M. Galia, and V. J. Cadiz, Appl. Polym. Sci., 99, 1367 (2006);
b) G. V. Plotnikova, S. F. Malysheva, N. K. Gusarova, A. K. Khalliulin, V. P. Udilov, and K. L.
(
Kuznetsov, Russ. J. Appl. Chem., 81, 304 (2008).
. (a) F. J. Alguacil and M. Alonso, Hydrometallurgy, 74(1–2), 157 (2004); (b) D. S. Flett,
Organomet. Chem., 690, 2426 (2005); (c) Z. Chan, Y. Yan-Zhao, Z. Tao, H. Jian, and L. Chang-
Hong, J. Radioanal. Nucl. Chem., 265, 419 (2005); (d) V. I. Menshikov, I. Yu. Voronova, O.
A. Proydakova, S. F. Malysheva, N. I. Ivanova, N. A. Belogorlova, N. K. Gusarova, and B. A.
Trofimov, Russ. J. Appl. Chem., 82, 183 (2009).
8. (a) S. P. Gubin, N. A. Kataeva, and G. B. Khomutov, Russ. Chem. Bull., 54, 827 (2005); (b) H.
Liu, J. S. Owen, and A. P. Alivisatos, J. Am. Chem. Soc., 129, 305 (2007).
9
. D. C. Gilheany and S. M. Mitchell, In The Chemistry of Organophosphorus Compounds, F. R.
Hartley, ed. (Wiley, New York, 1990), vol. 1, chap. 7, p. 1513190.
1
1
0. K. M. Pietrusiewicz, Phosphorus, Sulfur, and Silicon, 109–110, 573 (1996).
1. S. F. Malysheva, N. K. Gusarova, N. A. Belogorlova, A. V. Afonin, S. N. Arbuzova, and B. A.
Trofimov, Russ. Chem. Bull., 46, 1799 (1997).
1
2. (a) N. K. Gusarova, M. V. Bogdanova, N. I. Ivanova, N. A. Chernysheva, B. G. Sukhov, L.
M. Sinegovskaya, O. N. Kazheva, G. G. Alexandrov, O. A. D’yachenko, and B. A. Trofimov,
Synthesis, 3103 (2005); (b) B. G. Sukhov, N. K. Gusarova, N. I. Ivanova, M. V. Bogdanova, O.
N. Kazheva, G. G. Alexandrov, O. A. D’yachenko, L. M. Sinegovskaya, S. F. Malysheva, B.
A. Trofimov, J. Struct. Chem., 46, 1066 (2005); (c) S. N. Arbuzova, N. K. Gusarova, and B. A.
Trofimov, Arkivoc, v, 12 (2006).
1
3. B. A. Trofimov, A.V. Artem’ev, S. F. Malysheva, and N. K. Gusarova, J. Organomet. Chem.,
694, 4116 (2009).
1
1
4. E. B. Smart, ed., Organic Synthesis (Wiley, New York, 1989).
5. S. V. Fedorov, L. B. Krivdin, Yu. Yu. Rusakov, I. A. Ushakov, N. V. Istomina, N. A. Belogorlova,
S. F. Malysheva, N. K. Gusarova, and B. A. Trofimov, Magn. Reson. Chem., 46, 288 (2009).
6. A. Albert and E. Sergeant, In Ionization Constants of Acids and Bases, B. A. Koshits, Ed.
1
(Moscow, Leningrad, Khimiya, 1964) (in Russian).