Cycloaddition of primary phosphines to divinyl sulfide

Article abstract of DOI:10.1134/S107042801301003X

Primary phosphines reacted with divinyl sulfide under radical initiation conditions (AIBN, 65-70 C, reactant molar ratio 1:1) according to the addition-cyclization pattern to give 4-substituted 1,4-thiaphosphinanes which underwent almost quantitative oxid

Full text of DOI:10.1134/S107042801301003X

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2013, Vol. 49, No. 1, pp. 12–16. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © N.K. Gusarova, S.F. Malysheva, V.A. Kuimov, N.A. Belogorlova, A.V. Vashchenko, B.A. Trofimov, 2013, published in Zhurnal
Organicheskoi Khimii, 2013, Vol. 49, No. 1, pp. 22–26.
Dedicated to Full Member of the Russian Academy of Sciences
G.A. Tolstikov on his 80th anniversary
Cycloaddition of Primary Phosphines to Divinyl Sulfide
N. K. Gusarova, S. F. Malysheva, V. A. Kuimov, N. A. Belogorlova,
A. V. Vashchenko, and B. A. Trofimov
Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: boris_trofimov@irioch.irk.ru
Received November 23, 2012
Abstract—Primary phosphines reacted with divinyl sulfide under radical initiation conditions (AIBN, 65–
70°C, reactant molar ratio 1:1) according to the addition–cyclization pattern to give 4-substituted 1,4-thia-
phosphinanes which underwent almost quantitative oxidation with oxygen or elemental sulfur, yielding the
corresponding 4-substituted 1,4-thiaphosphinane oxides (sulfides). The reaction of 4-(2-phenylethyl)-1,4-thia-
phosphinane with methyl iodide afforded 4-methyl-4-(2-phenylethyl)-1,4-thiaphosphinanium iodide with high
chemoselectivity.
DOI: 10.1134/S107042801301003X
Phosphorus-and-sulfur-containing heterocycles, pri-
marily 1,2-thiaphospholanes [1–8] and 1,2-thiaphos-
phinates [1–8], attract interest as efficient antioxidant
additives to lubricating oils and polymers [9–11],
promising extractants for rare-earth and transuranium
elements [12], polydentate ligands for metal com-
plexes [1, 13–15], and building blocks for organic
synthesis [16–19].
bis(alkenyl)phosphonium bromides with sodium hy-
drogen sulfide [22, 24]. Cathodic reduction of bromide
IIIe gave 1,4-thiaphosphinane IIa in 56% yield [21].
The procedure proposed previously for the syn-
thesis of 4-phenyl-1,4-thiaphosphinane from divinyl
sulfide and phenylphosphine [20] turned out to be
inefficient. The reaction was carried with equimolar
amounts of the reactants under UV irradiation in di-
ethyl ether (30°C, 10 h), and the yield of thiaphos-
phinane Ia was as low as 5.7%. The reaction was
accompanied by formation of a compound which was
insoluble in diethyl ether, but neither composition nor
yield of this product was given in [20]. Thiaphos-
phinane Ia was almost quantitatively oxidized with
elemental selenium (50°C, benzene) to the correspond-
ing phosphine selenide Ib [20]. Conformational
analysis [25–27] showed that the heteroring in both Ia
and Ib adopts mainly chair conformation.
However, available data on the chemical properties
of 1,4-thiaphosphinanes and their derivatives are few
in number. 4-Phenyl-1,4-thiaphosphinane (Ia), 4-phe-
nyl-1,4λ5-thiaphosphinane 4-selenide (Ib) [20], 2,6-di-
methyl-4-phenyl-1,4-thiaphosphinane (IIa) and its
4-oxide IIb [21], and 1,4-thiaphosphinan-4-ium
bromides IIIa–IIIe [22–24] have been reported.
Compounds IIIa–IIIe were successfully used as
phase-transfer catalysts in the Finkelstein and Kolbe
reactions [23]; they were synthesized by reaction of
Me
R2
S
S
S
Br–
Ph
P
Ph
P
Ph
P
R1
Me
R3
X
X
Ia, Ib
IIa, IIb
IIIa–IIIe
I, X = LEP (a), Se (b); II, X = LEP (a), O (b); III, R1 = Ph, R2 = H, R3 = Me (a); R1 = R2 = R3 = Me (b); R1 = t-Bu,
R2 = R3 = Me (c); R1 = PhCH2, R2 = R3 = Me (d); R1 = Ph, R2 = R3 = Me (e).
12

CYCLOADDITION OF PRIMARY PHOSPHINES TO DIVINYL SULFIDE
13
The goal of the present work was to develop proce-
dures for the preparation of 4-substituted 1,4-thiaphos-
phinanes and their derivatives by reaction of primary
phosphines with divinyl sulfide. As starting com-
pounds we used octyl- and (2-phenylethyl)phosphines
IVa and IVb that can be readily obtained from red
phosphorus and octyl bromide or styrene in superbasic
medium [28–30].
yield by prolonged (35 h, 22–24°C) bubbling of
oxygen through a solution of Vb in chloroform. By
heating (50°C, 1 h) thiaphosphinane Vb with elemen-
tal sulfur in toluene we obtained 1,4λ5-thiaphosphinane
4-sulfide VIIb in almost quantitative yield (Scheme 3).
Thiaphosphinane Vb readily and chemoselectively
reacted with methyl iodide in diethyl ether (22–24°C,
1 h) to produce 87% of phosphonium iodide VIIIb.
According to the 31P NMR data, no alternative S-al-
kylation product, 1-methyl-4-(2-phenylethyl)-1,4-thia-
phosphinan-1-ium iodide, was formed (Scheme 4).
Primary phosphines IVa and IVb reacted with
divinyl sulfide in the presence of a catalytic amount of
AIBN as radical initiator (65–70°C, 30–40 h, reactant
molar ratio 1 : 1, argon) to produce 4-substituted
1,4-thiaphosphinanes Va and Vb in 51 and 89% yield,
respectively, with high chemo- and regioselectivity
(Scheme 1).
Scheme 4.
S
Ph
MeI, Et2O, 22–24°C, 1 h
I–
Vb
P
Me
VIIIb
Scheme 1.
S
AIBN, 65–70°C
RPH2
+
Phosphine generated together with hydrogen from
red phosphorus and potassium hydroxide in a water–
toluene system (60–70°C) [31] did not react with
divinyl sulfide under radical initiation conditions
(AIBN, 65°C, 4.5 h, argon). This reaction led to the
formation of a cross-linked polymer containing no
phosphorus (according to the data of elemental anal-
ysis). By passing a PH3–H2 mixture through a solution
of divinyl sulfide in 1,4-dioxane (AIBN, 65°C, 4.5 h,
argon) we obtained a polymeric material which was
insoluble in organic solvents and water; it contained
~5 wt % of phosphorus, which corresponds to a phos-
phine-to-divinyl sulfide ratio of 1:7.
S
H2C
CH2
P
R
Va, Vb
R = C8H17 (a), PhCH2CH2 (b).
The yield of Va was relatively low because of its
ready oxidation to phosphine oxide VIa with atmos-
pheric oxygen (Scheme 2). We failed to avoid this
process although all operations were performed under
argon. When a solution of Va in CDCl3 was kept in
an NMR ampule for 10 h at room temperature on
exposure to air, compound Va was quantitatively con-
verted into oxide VIa.
The relative stability and steric structure of
1,4-thiaphosphinanes were studied by quantum-chemi-
cal calculations. The calculations were performed at
the DFT/B3LYP level of theory with the use of
valence-split 6-311++G(d,p) basis set with account
taken of polarization and diffuse functions [32, 33]
(Gaussian 09 software package [34]). 4-Methyl-1,4-
thiaphosphinane (IX), 4-methyl-1,4λ5-thiaphosphinane
oxide (X), and 4-methyl-1,4λ5-thiaphosphinane sulfide
(XI) that are structurally related to heterocycles V–VII
were selected as model compounds. The results
showed that the most favorable conformer of IX–XI is
chair, which is consistent with the data reported for
Scheme 2.
O2, 22–24°C, 10 h
S
Va
C8H17
P
O
VIa
Under analogous conditions (CDCl3, room tempera-
ture, 11 h), thiaphosphinane Vb was oxidized to
4-(2-phenylethyl)-1,4λ5-thiaphosphinane 4-oxide
(VIb) only by 55% (according to the H and P NMR
data). The latter was synthesized in almost quantitative
1
31
Scheme 3.
X
P
Me
P
S8, 50°C, 1 h
S
Ph
Me
X
Vb
S
S
P
IXa–XIa
IXb–XIb
S
VIIb
IX, X = LEP; X, X = O; XI, X = S.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 1 2013

GUSAROVA et al.
14
[8H, (CH2)4Me], 1.39–1.68 m [4H, (CH2)2CH2P],
compounds Ia and Ib [25–27]. The energy of the chair
conformer is lower by 3.5–4.0 kcal/mol than that of the
boat conformer. The P=X bond in the chair con-
formers of IX–XI may have axial (a) or equatorial
orientation (b), the former being more advantageous.
The energy gain of the axial orientation of the P=X
bond increases in the series thiaphosphinane IX <
thiaphosphinane oxide X < thiaphosphinane sulfide XI
and is 0.75, 1.10, and 1.46 kcal/mol, respectively.
1.81–2.08 m (6H, CH2P), 2.59–2.78 m (4H, CH2S).
13C NMR spectrum, δC, ppm: 14.04 (Me), 19.89 (C7′),
2
22.61 (C6′), 23.40 (C4′), 25.50 d (CH2S, JPC
=
12.0 Hz), 25.98 d (C3′, JPC = 4.3 Hz), 29.20 d (PCH2,
3
1JPC = 13.7 Hz), 29.24 d (C1′, JPC = 12.6 Hz), 31.25 d
1
(C2′, JPC = 11.1 Hz), 31.81 (C5′). 31P NMR spectrum:
2
δP –27.66 ppm. Found, %: C 61.95; H 10.50; P 13.58;
S 13.22. C12H25PS. Calculated, %: C 62.03; H 10.84;
P 13.33; S 13.80.
Relatively small energy difference between the
axial and equatorial conformers suggests their com-
parable populations. Therefore, it was reasonable to
presume that the reactivity of the examined com-
pounds should be determined by orientation of the lone
electron pairs on the heteroatoms.
4-(2-Phenylethyl)-1,4-thiaphosphinane (Vb).
Yield 0.20 g (89%), viscous undistillable liquid.
1H NMR spectrum, δ, ppm: 1.71–1.73 m (6H, CH2P),
2.5–2.64 m (4H, CH2S), 2.71–2.74 m (2H, CH2Ph),
7.17–7.27 m (5H, Ph). 13C NMR spectrum, δC, ppm:
2
1
27.22 d (CH2S, JPC = 16.3 Hz), 28.82 d (CH2P, JPC
=
Thus we have developed a preparative procedure
for the synthesis of 4-substituted 1,4-thiaphosphinanes
via radical-initiated cycloaddition of primary alkyl-
and phenylalkylphosphines to divinyl sulfide. The
products are promising as bidentate ligands for the
design of new multipurpose metal complexes, special
metal-chelating extractants, and reactive building
blocks for organic synthesis.
1
18.4 Hz), 28.91 d (PhCH2CH2P, JPC = 14.6 Hz),
32.27 d (CH2Ph, JPC = 15.7 Hz), 126.03 (Cp), 128.0
2
(Cm), 128.41 (Co), 142.23 d (Ci, JPC = 10.3 Hz).
3
31P NMR spectrum, δP, ppm: –26.94. Found, %:
C 64.55; H 7.50; P 13.78; S 14.29. C12H17PS. Calcu-
lated, %: C 64.26; H 7.64; P 13.81; S 14.30.
4-Octyl-1,4λ5-thiaphosphinane 4-oxide (VIa).
A solution of 0.10 g (0.40 mmol) of thiaphosphinane
Va in 1 ml of CDCl3 was kept for 10 h on exposure to
atmospheric oxygen, and the solvent was removed.
EXPERIMENTAL
The 1H, 13C, and 31P NMR spectra were recorded on
a Bruker DPX-400 spectrometer at 400, 100, and
161.98 MHz, respectively, from solutions in CDCl3
using hexamethyldisiloxane (1H, 13C; internal) or
85% H3PO4 (31P, external) as reference. Compounds Ia
and Ib and divinyl sulfide were synthesized according
to the procedures reported in [28, 29, 35]. All experi-
ments were performed under argon. The reactions of
IVa and IVb with divinyl sulfide to obtain thiaphos-
phinanes Va and Vb were carried out in sealed
ampules.
1
Yield 0.10 g (93%), colorless oily substance. H NMR
2
spectrum, δ, ppm: 0.87 t (3H, Me, JHH = 6.3 Hz),
1.24–1.27 m (6H, 5′-H, 6′-H, 7′-H), 1.37–1.40 m (2H,
4′-H), 1.50–1.75 m (4H, 2′-H, 3′-H), 1.81–2.19 m (6H,
PCH2), 2.65–2.83 m (4H, CH2S). 13C NMR spectrum,
δC, ppm: 14.14 (Me), 20.09 (C7′), 22.66 (C6′), 24.03 d
and 25.06 d (CH2S, 2JPC = 6.0 Hz), 28.50 d (C5′, 4JPC
=
2
3.6 Hz), 30.45 d (C2′, JPC = 15.4 Hz), 30.75 d (C3′,
1
3JPC = 13.6 Hz), 31.55 (C4′), 31.75 d (PCH2, JPC
=
1
51.2 Hz), 32.59 d (C1′, JPC = 53.0). 31P NMR spec-
trum: δP 38.05 ppm. Found, %: C 58.55; H 10.50;
P 12.78; S 13.29. C12H25OPS. Calculated, %: C 58.03;
H 10.15; P 12.47; S 12.91.
Cycloaddition of primary phosphines to divinyl
sulfide (general procedure). An ampule was filled with
argon and charged with 1.0 mmol of phosphine IVa or
IVb, 1.0 mmol of divinyl sulfide, and 0.012 g (5 wt %)
of AIBN. The ampule was sealed and heated at 65–
70°C for 30 (IVa) or 40 h (IVb). The ampule was then
opened and evacuated for 1 h at a residual pressure of
1 mm on heating to 100°C, and the residue was
purified by passing through a 3-cm layer of aluminum
oxide using diethyl ether as eluent.
4-(2-Phenylethyl)-1,4λ5-thiaphosphinane 4-oxide
(VIb). Atmospheric air was bubbled over a period of
45 h through a solution of 0.20 g (0.89 mmol) of
thiaphosphinane Vb in 5 ml of chloroform, and the
solvent was removed. Yield 0.21 g (98%), colorless
1
oily substance. H NMR spectrum, δ, ppm: 1.81–
2.08 m (6H, PCH2), 2.81–2.99 m (4H, PhCH2), 7.20–
7.34 m (5H, Ph). 31P NMR spectrum: δP 45.12 ppm.
Found, %: C 60.25; H 7.30; P 12.78; S 13.19.
C12H17OPS. Calculated, %: C 59.98; H 7.13; P 12.89;
S 13.39.
4-Octyl-1,4-thiaphosphinane (Va). Yield 0.11 g
(51%), viscous undistillable liquid. 1H NMR spectrum,
2
δ, ppm: 0.86 t (3H, Me, JHH = 6.3 Hz), 1.25–1.41 m
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 1 2013

CYCLOADDITION OF PRIMARY PHOSPHINES TO DIVINYL SULFIDE
15
4-(2-Phenylethyl)-1,4λ5-thiaphosphinane 4-sul-
fide (VIIb). Powdered sulfur, 0.05 g (1.5 mmol), was
added to a solution of 0.33 g (1.5 mmol) of thiaphos-
phinane Vb in 3 ml of toluene, and the mixture was
stirred for 1 h at 50°C. The solvent was removed, the
oily residue was reprecipitated from chloroform into
hexane, and the precipitate was washed thrice with
diethyl ether and dried under reduced pressure. Yield
0.33 g (87%), light yellow powder, mp 98–99°C.
1H NMR spectrum, δ, ppm: 2.17 m (6H, PCH2),
2.84 m (4H, CH2S), 2.94 m (2H, CH2Ph), 7.23–7.29 m
(5H, Ph). 13C NMR spectrum, δC, ppm: 25.82 (CH2S),
δP 38.11, 39.79, 40.57, 42.62, 43.05, 46.96, 59.70,
63.46, 71.59, and 74.81 ppm. The precipitate (0.1 g)
was washed with water, acetone, alcohol, and hexane
and dried under reduced pressure. mp >290°C
(decomp.). IR spectrum (KBr): ν 1150 cm–1 (P=O).
Found, %: C 46.24; H 7.07; P 4.88; S 30.25.
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 11-03-00286) and by the Council for Grants at the
President of the Russian Federation (Program for
Support of Leading Scientific Schools, project
no. NSh-1550-2012.3).
1
29.29 (CH2Ph), 32.08 d (CH2P, JPC = 43.7 Hz),
1
34.28 d (CH2CH2Ph, JPC = 48.0 Hz), 127.47 (Cp),
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C 56.22; H 6.68; P 12.08; S 25.02.
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