Synthesis and characterization of O,O'-bis(α-naphthyl, β-naphthyl, and 2, 3, 5-trimethylphenyl)dithiophosphate ligands

Article abstract of DOI:10.1080/10426507.2012.680081

O,O-Bis(α-Naphthyl, β-Naphthyl and 2,3,5-trimethylphenyl) dithiophosphate ligands have been isolated as triethylammonium salts, (α-C₁₀H₇O-, β-C₁₀H₇O, and (CH₃)₃C₆H₂O)<

Full text of DOI:10.1080/10426507.2012.680081

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Phosphorus, Sulfur, and Silicon and the
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Synthesis and Characterization of O,O'-
Bis(α-Naphthyl, β-Naphthyl, and 2, 3,
5-Trimethylphenyl)Dithiophosphate
Ligands
Onkar Singh a , Mukhtyar S. Saini a , Jaya Dwivedi b & Aran Kumar a
a Department of Chemistry , Govt. G. M. Science College , Jammu ,
Jammu , 180001 , India
b Department of Chemistry , Banasthali University , Jaipur ,
Rajasthan , 304022 , India
Accepted author version posted online: 13 Apr 2012.Published
online: 06 Aug 2012.
To cite this article: Onkar Singh , Mukhtyar S. Saini , Jaya Dwivedi & Aran Kumar (2012) Synthesis and
Characterization of O,O'-Bis(α-Naphthyl, β-Naphthyl, and 2, 3, 5-Trimethylphenyl)Dithiophosphate
Ligands, Phosphorus, Sulfur, and Silicon and the Related Elements, 187:11, 1324-1330, DOI:
10.1080/10426507.2012.680081
To link to this article: http://dx.doi.org/10.1080/10426507.2012.680081
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Phosphorus, Sulfur, and Silicon, 187:1324–1330, 2012
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2012.680081
SYNTHESIS AND CHARACTERIZATION OF
O,O’ -BIS(α-NAPHTHYL, β-NAPHTHYL, AND 2, 3,
5-TRIMETHYLPHENYL) DITHIOPHOSPHATE LIGANDS
Onkar Singh,1 Mukhtyar S. Saini,1 Jaya Dwivedi,2
and Aran Kumar1
1Department of Chemistry, Govt. G. M. Science College, Jammu,
Jammu, 180001, India
2Department of Chemistry, Banasthali University, Jaipur, Rajasthan,
304022, India
GRAPHICAL ABSTRACT
Abstract O,Oꢁ-Bis(α-Naphthyl, β-Naphthyl and 2,3,5-trimethylphenyl) dithiophosphate
ligands have been isolated as triethylammonium salts, (α-C10H7O-, β-C10H7O, and
(CH3)3C6H2O)2PS2HNEt3, by the reaction of α-C10H7OH, β-C10H7OH, or (CH3)3C6H2OH
with P2S5 in presence of Et3N, in 4:1:2 molar ratio in chloroform under anhydrous conditions.
Acidic form of these ligands, (α-C10H7O-, β-C10H7O-, or (CH3)3C6H2O)2PS2H, have been
obtained by the direct reaction of α-C10H7OH, β-C10H7OH-, or (CH3)3C6H2OH with P2S5
in 4:1 molar ratio in presence of microwaves under solvent-free conditions. Both forms of the
ligands have been converted into corresponding sodium salts, (α -C10H7O-, β-C10H7O-, or
(CH3)3C6H2O)2PS2Na. These compounds have been characterized by elemental analyses
(C, H, N, and S) and mass, IR, and NMR (1H, 13C and 31P) spectroscopic studies.
Supplemental materials are available for this article. Go to the publisher’s online edition of
Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
Keywords α-naphthyl; β-naphthyl; 2,3,5-trimethylphenyl; dithiophosphates; triethylammo-
nium
INTRODUCTION
O,Oꢁ-dialkyl dithiophosphate, (RO)2PS2X, and O,Oꢁ-alkylene dithiophosphate lig-
ands, OGOPS2X, (R = Me, Et, Prn, Pri, But or o, m, or p-Cresyl; G = -CH2CMe2CH2-,
-CH2CEt2CH2-, -CMe2CH2CHMe- or -CMe2CMe2-; X = H, Na, NH4 or Et3NH) occupy
Received 3 January 2012; accepted 17 March 2012.
One of the authors (A. Kumar) is grateful to University Grants Commission, New Delhi, for financial
support.
Address correspondence to Aran Kumar, Department of Chemistry, Govt. G. M. Science, College, Canal
Road Jammu, Jammu, 180001, India. E-mail: kumararana@gmail.com
1324

SYNTHESIS OF DITHIOPHOSPHATE LIGANDS
1325
a unique position as versatile chelating ligands.1–5 These ligands are known to form a
variety of complexes with transition and nontransition elements.2–12 Studies over the last
few decades have shown that these dithio-ligands have a tendency for different coordina-
tion patterns, by involving the sulfur atom in primary or secondary (intra or intermolecular)
bonds.2–4 In general, a bidentate nature of these ligands have been established.7–10 However,
they have also depicted other bonding modes, e.g., monodentate,11,12 anisobidentate,6,13 and
bridging.14 Various dithiophosphate complexes find extensive applications in medicines15 as
catalysts in asymmetric synthesis,16 agriculture,17,18 sol-gel processing,19 antiwear additives
to gear and motor oils,20 as heat stabilizers for polymers,21 extraction,22 and analytical pro-
cesses.23 A literature survey revealed that a substantial amount of work has been carried out
with these ligands but scant information is available on the systematic synthesis and charac-
terization of O,Oꢁ-bis(α-naphthyl, β-naphthyl, and 2,3,5-trimethylphenyl)dithiophosphate
ligands.24,25 Therefore, it was thought worthy to investigate the chemistry of O,Oꢁ-bis(α-
naphthyl, β-naphthyl, and 2,3,5-trimethylphenyl)dithiophosphates, by synthesizing them
in different reactive forms, which can be used to produce a variety of new dithiophosphate
derivatives in the future. We herein report, the synthesis and characterization of O,Oꢁ-bis(α-
naphthyl, β-naphthyl, and 2,3,5-trimethylphenyl) ligands as their acids, triethylammo-
nium, and sodium salts corresponding to (α-C10H7O-, β-C10H7O-, or (CH3)3C6H2O)2PS2
H/Et3NH/Na.
RESULTS AND DISCUSSION
During the present course of investigation, the direct reaction of P2S5 with α-naphthol,
β-naphthol or 2,3,5-trimethylphenol did not give quantitative yield of acidic form of O,Oꢁ-
bis(α-naphthyl, β-naphthyl or 2,3,5-trimethylphenyl) dithiophosphate ligands, α-C10H7O-,
β-C10H7O-, or (CH3)3C6H2O)2PS2H, under conventional method. The reaction rate was
so slow that only 35%–45% of reaction took place even after refluxing the reaction mixture
in toluene or chloroform for 24 h.
But it was found that the reaction of P2S5 with α-naphthol, β-naphthol or 2,3,5-
trimethylphenol takes place in presence of microwaves easily to produce the acidic form
of the ligands α-C10H7O-, β-C10H7O-, or (CH3)3C6H2O)2PS2H in ∼99% yield and in
drastically reduced time (Scheme 1).
Microwave, 750 W
4ROH +
2(RO)2PS2H + H2S
P2S5
230-250 Sec.
(1-3)
Scheme 1
Triethylammonium salts (α-C10H7O-, β-C10H7O-, and (CH3)3C6H2O)2PS2HNEt3)
of ligands were obtained by the reaction of P2S5 with α-naphthol, β-naphthol or 2,3,5-
trimethylphenol in presence of triethylamine, Et3N, in chloroform at in 15–20 min at
30 ◦C, as colorless sticky solids (Scheme 2).
CHCl3, 30 oC
2(RO)2PS2HNEt3 + H2S
4ROH + P2S5 + 2Et3N
15-20 Min.
(4-6)
Scheme 2

1326
O. SINGH ET AL.
Since the reactions of alcohols and phenols with P2S5 are reported to complete in
3–6 h, therefore, it is implicated that Et3N has not only acted as a reactant but also played
a catalytic role in these reactions.1–3
A literature survey reveals that benzene or toluene have been used as solvents for the
synthesis of dithiophosphate ligands,1,5 but we have found that the use of chloroform as a
solvent not only increases yield but reduces reaction time as well.
All these compounds (1–6) were easily converted to corresponding sodium salts,
α-C10H7O-, β-C10H7O-, or (CH3)3C6H2O)2PS2Na, by their direct reaction with sodium
metal in a 1:1 molar ratio in toluene at 40 ◦C as white powders (Scheme 3).
Toluene,40oC
(RO)2PS2H
+
Na
(RO)2PS2Na
-1/2 H2
o
Toluene,
40 C
(RO)2PS2HNEt3
+ Na
(RO)2PS2Na
(7-9)
-Et3N, 1/2 H2
Scheme 3
Compounds (1–6) are soluble in dichloromethane, chloroform, methanol, and ethanol,
sparingly soluble in benzene and toluene and insoluble in n-hexane and carbon tetra-
chloride. Compounds (7–9) are soluble in methanol and ethanol, sparingly soluble in
dichloromethane and chloroform but insoluble in benzene and toluene.
The micro elemental analyses (C, H, N, and S) of all the above compounds 1–9 were
found consistent to their molecular composition. A monomeric nature of the compounds
1–3 has been found by their molecular weight determinations in freezing benzene.
Infrared (IR) spectra were recorded in the range 4000–200 cm−1 and the tentative
assignments were done on the basis of relevant literature reports.1–5 IR spectra have shown
a broad absorption for νNH vibrations in the region 3581–3575 cm−1 for the compounds
4–6 while these absorptions were absent in the compound 1–3 and 7–9.5 In compounds 1–3,
the absorption for νSH vibration were observed at 3311–3298 cm−1, while these absorption
band are absent in compounds 4–6 and 7–9.1 In all the compound−s1ν(P)-O-C and νP-O-
(C) stretching vibrations were found in the region 1190–1108 cm and 950–886 cm−1
,
respectively.1 The bands in region 570–539 cm−1 and 718–682 cm−1 may be assigned to
for νP-S and νP S (symmetric and asymmetric) vibrations. The νCH stretching vibrations
of aromatic group appeared in the region 2950–2910 cm.−1
1
In the H NMR spectra, a triplet and quartet were observed for -CH3 and -CH2
protons of Et3N moiety in the compound 4–6 at δ1.25–1.28 (J = 7.2 Hz) and δ 3.09–3.11,
respectively. The chemical shift for -SH and -NH protons in the compounds 1–3 and
4–6 appeared at δ 4.52–4.55 and 9.24–9.27, respectively. The chemical shifts of -CH3
(attached to benzene ring) for compounds 3, 6, and 9 was recorded at δ 2.12–2.14. Multiple
characteristics for ring protons were observed at δ 6.93–7.45 for compounds 1–9.
The 13C NMR spectral study of the sodium salts 7–9 was not possible due to their
poor solubility in CDCl3. However, in 13C NMR spectral data of compounds 4–6, the
chemical shifts for -CH3 and -CH2 carbons of Et3NH moiety were observed in the region
δ8.5 and δ46.1–46.2, respectively. This up-field shift is due to positive charge on nitrogen.
For the compounds 3 and 6, the chemical shifts for the -CH3 carbons present on aromatic
ring were found at δ9.9–24.2. The chemical shifts C-O carbon for compounds 1–6 were

SYNTHESIS OF DITHIOPHOSPHATE LIGANDS
1327
found at δ151.4–151.1. The appearance of a chemical shift for C-O carbon without up-field
shift shows lack of intramolecular hydrogen bonding between protons attached to ortho
carbons of ring and oxygen atom attached to phosphorus atom.5,26 The chemical shifts for
remaining five ring carbons were found in the region δ116.2–145.2.
The chemical shifts of 31P NMR spectra (proton-decoupled) have been observed
as singlet for all compounds 1–9 the region δ84.6–109.7. The acidic form of the ligands
1–3 shows a peak as singlet in the region δ84.6–85.0, which suggests association of
proton with only one of the two sulfur atoms and partial covalent character for these
compounds. For triethylammonium 4–6 and sodium salts 7–9 singlet were observed in the
region δ102.9–103.3 and 109.4–109.7, which suggest ionic character of these compounds.
Occurrence of a singlet in each case shows that only one type of chemically bonded
phosphorus atom is present in all these compounds.27 Representative spectra for compound
3 (1H, 13C, and 31P NMR) are shown in Figures S1–S3 (Supplemental Materials)
EXPERIMENTAL
General Procedures and Reagents
All the experimental work was carried out strictly under anhydrous conditions, ni-
trogen atmosphere, and by using modified Schlenk techniques. Triethylamine (Sd Fine
◦
Chem., b.p. 88.8 C) was freshly distilled prior to use; chloroform and toluene were
dried by refluxing over phosphorus pentoxide and sodium metal, respectively, and were
kept under a nitrogen atmosphere. Naphth-1-ol, naphth-2-ol (Sd Fine Chem.), 2,3,5-
trimethylphenol(Aldrich), and phosphorus pentasulfide (MERCK) were procured commer-
cially and were used as such. Micro elemental analysis (C, H, and N) was done on Vario
EL III elemental analyzer while sulfur was estimated as BaSO4 by messenger’s method.
Infrared spectra were recorded in KBr on FTIR Perkin Elmer-377 spectrophotometer. The
1H and 13C NMR spectra were measured on Jeol FX 90Q 90 MHz using TMS as external
reference. The 31P NMR spectra were recorded by means of a Brucker DRX 300 (120 MHz)
using 85% H3PO4 as external reference. The mass spectrophotometeric analysis (EI) was
carried out on ESQUIRE-300 (Brucker–Daltonics).
Synthesis
(α-C10H7O)2PS2H (1). Naphth-1-ol (1.15 g, 8.0 mmol) and P4S10 (0.44 g,
1.0 mmol) were ground with a mortar in a glove box. Then this mixture was transferred
to a 50 mL beaker and subsequently subjected to microwave irradiations at 750 W. After
160 seconds of irradiation, the evolution of white fumes of H2S was observed, which
subsided within 15–20 s and a clear, colorless, thick liquid was obtained after 240 seconds.
This thick liquid converted to a pasty material upon cooling without any change in color.
Yield 1.51 g (99.3%); MW Calc./found: 382.44/376.47; MS(EI, m/z): 383.02 (21%, M+),
238.50 (100%); Anal. Calcd. for C20H15O2PS2 (382.44): C, 62.81; H, 3.95; S, 16.77;
%. Found: C, 62.78; H, 3.94; S, 16.73%. IR (KBr, cm−1): 3298b, 2938b, 1615m, 1502s,
1488s, 1188s, 945s, 710s, 557s; 1H NMR (CDCl3): δ4.52 (s, 1H, -SH), 7.0–7.38 (m, 14H,
-C10H7); 13C NMR (CDCl3): δ151.1, 145.2, 141.1, 134.1, 126.1, 124.3, 122.2, 121.0,
118.9, 116.2; 31P NMR (CDCl3): δ84.6(s).
(β-C10H7O)2PS2H (2). The procedure adopted for the synthesis of 2 was similar
to those used for 1. For this reaction, naphth-2-ol (2.30 g, 16 mmol) and P4S10 (0.88 g,

1328
O. SINGH ET AL.
2.0 mmol) were used, product 2 was obtained as colorless pasty material in 230 s. Yield
3.01 g (99.0%); MW Calc./found: 382.44/376.78; MS(EI, m/z): 383.02 (21%, M+), 238.50
(100%); Anal. Calcd. for C20H15O2PS2: C, 62.81; H, 3.95; S, 16.77%. Found: C, 62.79;
H, 3.91; S, 16.73%. IR (KBr, cm−1): 3311b, 2940b, 1615m, 1502s, 1488s, 1190s, 950s,
712s, 562s; 1H NMR (CDCl3): δ4.53 (s, 1H, -SH), 6.98–7.45 (m, 14H, -C10H7); 13C NMR
(CDCl3): δ151.1, 144.9, 142.0, 134.7, 126.1, 123.3, 121.9, 120.8, 118.6, 116.2; 31P NMR
(CDCl3): δ84.6(s).
[2,3,5-(CH3)3C6H2O)]2PS2H (3). A similar synthetic procedure, as in the cases of
1 or 2, was used for the preparation of 3. For the reaction, 2,3,5-trimethylphenol (1.08 g,
8.0 mmol) and P4S10 (0.44 g/1.0 mmol) were used and product 3 was obtained as colorless
pasty material in 250 s. Yield 1.45 g (99.3%); MW Calc./found: 366.48/356.51; MS(EI,
m/z): 367.09 (21.4%, M+), 231.0 (100%); Anal. Calcd. for C18H23O2PS2: C, 58.99; H,
6.33; S, 17.50%. Found: C, 58.92; H, 6.31; S, 17.47%. IR (KBr, cm−1): 3317b, 2939b,
1
1618m, 1522s, 1488s, 1178s, 946s, 718s, 550s; H NMR (CDCl3): δ2.12 (s, 18H, -CH3
on ring, 4.55 (s, 1H, -SH), 6.93–7.40 (m, 4H, -C6H2); 13C NMR (CDCl3): δ151.2, 135.2,
132.1, 128.5, 126.1, 124.3, 24.2(C-5 -CH3), 18.3(C-3 -CH3), 9.9 (C-2 -CH3); 31P NMR
(CDCl3): δ85.0(s).
(α-C10H7O)2PS2HNEt3 (4). A chloroform solution (∼40 mL) of naphth-1-ol
(11.53 g, 80.0 mmol) was added dropwise to a chloroform (∼100 mL) suspension of
P4S10 (4.44 g, 10.0 mmol). After stirring the contents for 3–5 min at ∼35 ◦C, a chloroform
solution (∼50 mL) of Et3N (5.56 mL, 40.0 mmol) was added dropwise to it. All the P2S5
reacted in 15–20 min and a clear solution was obtained. Evaporation of excess of chlo-
roform under reduced pressure resulted to compound 4 in quantitative yield as colorless
◦
sticky solid. Yield 18.7 g (97.3%); mp: 66 C; MS(EI, m/z): 484.15 (28%, M+), 382.96
(100%); Anal. Calcd. for C26H30O2PS2N: C, 64.57; H, 6.25; N, 2.90; S, 13.26% Found: C,
64.29; H, 6.20; N, 2.80; S, 13.22. IR (KBr, cm−1): 3579b, 2930b, 1621m, 1511s, 1475s,
1
1181s, 901s, 699s, 545s; H NMR (CDCl3): δ1.25 (t, 9H, -CH3 of Et3N, J = 7.2 Hz),
3.10 (m, 6H, -CH2 of Et3N), 6.99–7.42 (m, 14H, -C10H7), 9.25 (s, 1H, -NH); 13C NMR
(CDCl3): δ151.1, 145.2, 141.3, 134.1, 126.1, 124.3, 122.2, 121.1, 118.5, 116.2, 46.1(-CH2-
of Et3NH), 8.5(-CH3 of Et3NH); 31P NMR (CDCl3): δ102.9(s).
(β-C10H7O)2PS2HNEt3 (5). The procedure adopted for the synthesis of 5 was
similar to that used for 4. For this reaction, naphth-2-ol (1.15 g, 8.0 mmol), P4S10 (0.44 g,
1.0 mmol), and Et3N (0.55 mL, 4.0 mmol) ◦were used and product 5 was obtained colorless
sticky solid. Yield 1.87 g (98%); mp: 68 C; MS (EI, m/z): 484.15 (28%, M+), 382.96
(100%); Anal. Calcd. for C26H30O2PS2N: C, 64.57; H, 6.25; N, 2.90; S, 13.26% Found: C,
64.29; H, 6.20; N, 2.80; S, 13.22. IR (KBr, cm−1): 3580b, 2922b, 1617m, 1528s, 1487s,
1
1185s, 909s, 695s, 543s; H NMR (CDCl3): δ1.25 (t, 9H, -CH3 of Et3N, J = 7.2 Hz),
3.11 (m, 6H, -CH2 of Et3N), 6.95–7.32 (m, 14H, -C10H7), 9.24 (s, 1H, -NH); 13C NMR
(CDCl3): δ151.2, 145.2, 141.1, 134.1, 126.1, 124.3, 122.2, 121.0, 118.9, 116.2; 46.2 (-CH2-
of Et3NH), 8.5 (-CH3 of Et3NH); 31P NMR (CDCl3): δ103.0(s).
[2,3,5-(CH3)3C6H2O)]2PS2Et3NH (6). A similar synthetic procedure as in the
cases of 4 or 5 was used for the preparation of 6. 2,3,5-Trimethylphenol (1.08 g, 8.0 mmol),
P2S5 (0.44 g, 1.0 mmol) and Et3N (0.55 mL, 4.0 mmol) were ◦used and product 3 was
obtained as colorless sticky solid. Yield 12.16 g (98%); mp: 63 C; MS(EI, m/z): 468.21
(27%, M+), 367.02 (100%); Anal. Calcd. for C24H38O2PS2N: C, 61.64; H, 8.19; N, 3.00;
S, 13.71%. Found: C, 61.58; H, 8.15; N, 2.97; S, 13.63%. IR (KBr, cm−1): 3575b, 2910b,
1619m, 1512s, 1496s, 1143s, 911s, 682s, 544s; 1H NMR (CDCl3): δ1.28 (t, 9H, -CH3 of
Et3N, J = 7.2 Hz), 2.12 (s, 18H, -CH3 on ring), 3.09 (m, 6H, -CH2 of Et3N), 6.98–7.45

SYNTHESIS OF DITHIOPHOSPHATE LIGANDS
1329
(m, 8H, -C6H2), 9.27 (s, 1H, -NH); 13C NMR (CDCl3): δ151.4, 135.1, 132.0, 128.5, 126.1,
126.3, 46.2 (-CH2- of Et3NH), 24.1(C-5 -CH3), 18.4(C-3 -CH3), 9.8 (C-2 -CH3), 8.5 (-CH3
of Et3NH); 31P NMR (CDCl3): δ 103.3(s).
(α-C10H7O)2PS2Na (7). The solution of compound 1, (3.82 g,10.0 mmol) or com-
pound 4, (4.83 g,10.0 mmol) was prepared in toluene (100 mL) at 40 ◦C. To this solution,
was added sodium metal (0.23 g, 10.0 mmol) and this reaction mixture was stirred at 40 ◦C
for 3 h under anhydrous conditions. White precipitates so formed were filtered through a
funnel fitted with G-4 sintered disc. Finally, the residue was dried under reduced pressure
that gave the compound 7 as white solid. Yield: 3.58 g (88.55%) and 3.60 g (88.88%) with
compounds 1 and 4, respectively; mp: 98 ◦C; MS(EI, m/z): 405.01 (21.60%, M+), 238.86
(100%); Anal. Calcd. For C20H14O2PS2Na: C, 59.40; H, 3.49; S, 15.86%. Found: C, 59.20;
H, 3.47; S, 15.78. IR (KBr, cm−1): 2918b, 1624m, 1509s, 1497s, 1120s, 890s, 685s, 546s;
1H NMR (CDCl3): δ6.98–7.29 (m, 14H, -C10H7); 31P NMR (CDCl3):δ109.4(s).
(β-C10H7O)2PS2Na (8). Same synthetic procedure as in case of 7 was also used for
8, for this reaction, compound 2, (4.23 g, 10.0 mmol) or compound 5, (4.83 g, 10.0 mmol)
and sodium metal (0.23 g,10.0 mmol) were used. Compound 8 was obtained as white
solid. Yield: 3.59 g (88.78%) and 3.62 g (89.38%) with compounds 2 and 5, respec-
tively; mp: 97 ◦C; MS(EI, m/z): 405.01 (21.60%, M+), 238.86 (100%); Anal. Calcd. for
C20H14O2PS2Na: C, 59.40; H, 3.49; S, 15.86%. Found: C, 59.20; H, 3.47; S, 15.78. IR
1
(KBr, cm−1): 2915b, 1618m, 1522s, 1498s, 1125s, 886s, 690s, 539s; H NMR (CDCl3):
δ6.95–7.38 (m, 14H, -C7H10); 31P NMR (CDCl3): δ109.5(s).
[2,3,5-(CH3)3C6H2O)]2PS2Na (9). Themethod usedfor synthesis of 9 was same as
used for compounds 7 and 8, for this reaction, compound 3, (3.66 g,10.0 mmol) or compound
5, (4.67 g,10.0 mmol), and sodium metal (0.23 g,10.0 mmol) were used. Compound 9 was
obtained as white solid. Yield: 3.37 g (88.6%) and 3.38 g (86.3%) with compounds 3 and 6,
respectively; mp: 95 ◦C; MS(EI, m/z): 389.07 (19.5%, M+), 222.92 (100%); Anal. Calcd.
for C18H22O2PS2Na: C, 55.65; H, 5.71; S, 16.51%. Found: C, 55.61; H, 5.69; S, 16.49%.
IR (KBr, cm−1): 2930b, 1625m, 1529s, 1499s, 1108s, 898s, 700s, 544s; 1H NMR (CDCl3, δ
ppm): 2.14 (s, 18H, -CH3 on ring), 6.98–7.45 (m, 4H, -C6H2); 31P NMR (CDCl3): δ109.7(s).
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