2-Ethoxy-2,3-dihydro[d][1,2]oxaphosphole 2-oxide in the synthesis of dialkyl(diaryl)(2-hydroxybenzyl)phosphine oxides

Article abstract of DOI:10.1134/S1070363216030063

A facile method of synthesis of functionally substituted P(IV) derivatives―dialkyl(diaryl)(2-hydroxybenzyl) phosphine oxides―by the reaction of 2-ethoxy-2,3-dihydro[d][1,2]oxaphosphole 2-oxide with organomagnesium compounds, which allows wide variation of

Full text of DOI:10.1134/S1070363216030063

ISSN 1070-3632, Russian Journal of General Chemistry, 2016, Vol. 86, No. 3, pp. 530–533. © Pleiades Publishing, Ltd., 2016.
Original Russian Text © D.A. Tatarinov, D.M. Kuznetsov, A.A. Kostin, V.F. Mironov, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 3,
pp. 386–390.
To the 100th Anniversary of A.N. Pudovik
2-Ethoxy-2,3-dihydro[d][1,2]oxaphosphole 2-Oxide
in the Synthesis of Dialkyl(diaryl)(2-hydroxybenzyl)phosphine
Oxides
D. A. Tatarinov, D. M. Kuznetsov, A. A. Kostin, and V. F. Mironov
Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences,
ul. Akademika Arbuzova 8, Kazan, Tatarstan, 420088 Russia
e-mail: datint@iopc.ru
Received January 25, 2016
Abstract—A facile method of synthesis of functionally substituted P(IV) derivatives―dialkyl(diaryl)(2-hydroxy-
benzyl)phosphine oxides―by the reaction of 2-ethoxy-2,3-dihydro[d][1,2]oxaphosphole 2-oxide with organo-
magnesium compounds, which allows wide variation of substituents on the phosphorus atom was developed.
Keywords: phosphine oxides, dihydrobenzophospholes, phosphonates, Grignard reagent, salicyl alcohol
DOI: 10.1134/S1070363216030063
Phosphine oxides are one of the most widely used
organophosphorus compounds. They are used as
extractants [1, 2], ligands for metal complex catalysts
[3–5] and photoluminescent complexes [6–8], аs well
as organocatalysts [9, 10]. Phosphine oxides contain-
ing substituents with carbonyl [11–14] or hydroxy
groups [15, 16] can extend the range of potential
applications of this class of compounds.
The starting benzophosphole 1 was prepared by the
reaction of salicyl alcohol with triethyl phosphate as
described in [24].
OH
O
O
Δ, PhMe
P(OEt)3
+
P
OH
OEt
1
Compound 1 was reacted with organomagnesium
compounds in a 1 : 2 ratio in THF to obtain dialkyl-
(diaryl)(2-hydroxynenzyl)phosphine oxides 2a–2d in
53–63% yields.
One of the most facile and convenient synthetic
approaches to phosphine oxides is based on reactions
of phosphorus acid halides with organomagnesium
compounds to form a P–C bond [17–19]. These
reactions allow one to synthesize only simple trialkyl-
or triarylphosphine oxides containing no additional
functionalities. Reactions of five- and six-membered
phosphorus heterocycles already containing one P–C
bond with organomagnesium compounds allow to
synthesize a functionally substituted phosphine oxides
with oxoalkyl [20], hydroxyvinyl [21], and hydroxy-
phenyl fragments [22, 23].
4
OH
3
O
O
2RMgBr
5
6
O
R
P
P
OEt
2
R
7
2 1
1
R = Et (2а), Pr (2b), Bu (2b), Ph (2d).
Phosphine oxides 2a, 2c, and 2d were previously
prepared by the reactions of ethyl dialkyl- [25, 26] or
diarylphosphinoites [25, 27] with salicyl alcohol.
However, the synthesis of phosphine oxide 2a is
described in the patent [25], where no its physico-
chemical and spectral characteristics are given.
In the present work we describe a facile method of
synthesis of dialkyl(diaryl)(2-hydroxybenzyl)phos-
phine oxides by the reaction of 2-ethoxy-2,3-dihydro-
[d][1,2]oxaphosphole 2-oxide (1) with organomag-
nesium compounds.
The lower yields of phosphine oxides 2а–2d in the
reactions of benzophosphole 1 with organomagnesium
530

2-ETHOXY-2,3-DIHYDRO[d][1,2]OXAPHOSPHOLE 2-OXIDE
3JHН = 7.5
531
3JHН = 7.4
4JHН = 1.3
3JHН = 8.0
4JHН = 7.5
4JHН = 1.5
6JPН = 1.7
3JHН = 8.0
4JHН = 1.3
3JHН = 7.4
4JHН = 1.5
4JPН = 1.7
5JPН = 1.1
δ, ppm
Downfield regions of the 1Н and 1Н–{31P} NMR spectra (400 MHz, СDCl3) of phosphine oxide 2a.
compounds compared with those in the published
syntheses of dialkyl(diaryl)(2-methyl-4-oxopent-2-yl)-
phosphine oxides [20] or (Z)-4-[dialkyl(diphenyl)-
phosphoryl]-2-methylbut-3-en-1-ols [21], are, probably,
explained by a lower reactivity of the exocyclic Р–О
bond in compound 1 in these reactions.
Thus, the alkyl carbon atoms directly attached to
phosphorus appear as a doublet (1JРС = 64–66 Hz) at
19–29 ppm in the 13С–{1Н} NMR spectra. The РС1
carbon signal is observed at 32–33 ppm (1JРС ~ 61 Hz).
The ipso-carbon atoms С2 and С3 give weak signals at
119.9 and 156.5 ppm, respectively. The С4 and С6
signals appear very close to each other, and they are
difficult to differentiate by the chemical shift and
multiplicity (~119.5 and ~120 ppm). The С5 carbon
appears as a a doublet of doublet of doublets near
The structure of the synthesized (hydroxybenzyl)-
1
phosphine oxides was confirmed by IR and 31Р, Н,
and 13С NMR spectroscopy. The benzyl methylene
1
proton signals in the Н NMR spectra of phosphine
3
5
129 ppm (1JСH = 160–161, JНС ~ 8.5, JРС = 1.8 Hz),
and the С7 carbon signal is observed near 130 ppm as a
doublet of multiplets (1JHC = 156–157, 3JРС = 5–6 Hz).
oxides 2а–2d appear as a characteristic doublet at
δ = 3.15 ppm, 2JPH = 11.9 Hz (2d, δ = 3.84 ppm, 2JРН
=
13.7 Hz). The phenyl proton signals were assigned as
we further exemplify by the assignments for
compound 2а. The figure shows the aromatic parts of
The most characteristic band in the IR spectra of
compounds 2а–2d is a strong and broad OH stretching
absorption band above 3000 cm–1.
1
1
the H and H–{31P} NMR spectra (400 MHz, CDCl3)
of this compound. The hydroxybenzyl H6 proton in the
1Н–{31P} NMR spectrum resonates in the farthest
downfield region of the aromatic part of the spectrum
as a doublet of doublet of doublets at 6.85 ppm, which
Thus, we developed a facile method of synthesis of
dialkyl(diaryl)(2-hydroxybenzyl)phosphine oxides by
the reaction of 2-ethoxy-2,3-dihydro[d][1,2]oxaphos-
phole 2-oxide with organomagnesium compounds,
which allows one to widely vary substituents on the
phosphorus atom.
1
in the Н NMR spectrum appears as a doublet of
3
doublet of doublet of doublets (3JНН1 = 7.5, JНН = 7.4,
5
4JНН = 1.3, JPН = 1.1 Hz). In the Н–{31P} spectrum
the H7 proton appears as doublet of doublets at
7.0 ppm; in the 1Н spectrum this signal transforms into
a doublet of doublet of doublets (3JНН = 7.4, 4JHН = 1.5,
4JPН = 1.7 Hz). The H4 appears as a doublet of doublets
EXPERIMENTAL
1
13
13
The Н, С, С–{1H}, and 31Р–{1H} NMR spectra
were measured on a Bruker Avance-400 spectrometer
[400 (1Н), 160.9 (31Р), and 100.6 MHz (13С)] against
solvent signals. The IR spectra were obtained on a
Bruker Vector-22 instrument for suspensions in
mineral oil, thin films between KBr plates, or KBr
pellets. The melting points were measured using a
Boetius hot stage.
4
at ~7 ppm (3JHН = 8.0, JНН = 1.3 Hz). The H5 appears
as a doublet of doublet of doublets at 7.2 ppm in the
1Н–{31P} spectrum and as a doublet of doublet of
3
doublet of doublets (3JHН = 8.0, JНН = 7.5, 4JНН = 1.5,
6JPН = 1.7 Hz) in the 1H NMR spectrum.
The signals which are the easiest to identify in the
13С and 13С–{1Н} NMR spectra of phosphine oxides
2а–2d belong to carbons spin-coupled to phosphorus.
2-Ethoxy-2,3-dihydro[d][1,2]oxaphosphole 2-oxide
(1). A mixture of 20.0 g (0.1611 mol) о-hydroxybenzyl
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 3 2016

532
TATARINOV et al.
alcohol and 26.8 g (0.161 mol) of triethyl phosphite in
40 mL of toluene was heated under reflux for 12 h.
The solvent was removed, and the residue was heated
in a vacuum (80°С, 20 mmHg) and then distilled in a
vacuum of 0.03 mmHg at 113–116°С. Yield 24.3 g
(76%). 31Р–{1H} NMR spectrum: δP 46.0 ppm. The
physicochemical characteristics of the product are
consistent with those reported in [24, 28].
906, 939, 970, 1040, 1082, 1128, 1251, 1275, 1308,
1347, 1381, 1401, 1457, 1487, 1506, 1598, 2624,
2736, 2874, 2933, 2963, 3067. Н NMR spectrum
1
(CDCl3), δ, ppm (J, Hz): 1.05 t.d (6H, PCH2CH2CH3,
4
3JНН = 7.2, JРН = 1.0), 1.55–1.70 m (4H, PCH2CH2,
AB part of the АВХ system), 1.7–1.8 m (4H, PCH2,
2
AB part of the АВХ system), 3.15 d (2H, H1, JPН
=
12.0), 6.86 br.d.d (1H, H6, 3JHН = 7.6, 3JHН = 7.1), 6.97
d.d.d (1H, H7, JHН = 7.6, JHН = 1.8, JPН = 1.5), 7.02
3
4
4
d.d (1Н, Н4, JHН = 8.1, JHН = 1.3), 7.20 d.d.d.d (1Н,
Н5, 3JНН = 7.9, 3JНН = 7.4, 4JHН ~ 1.8, 6JPН = ~ 1.6). 13C
NMR spectrum (CDCl3), δC, ppm (J, Hz): 15.54 t.m
(d) (PCH2CH2, 1JHC = 129.7, 2JРС = 3.9), 15.86 br.q.d.t
3
4
Synthesis of dialkyl(diaryl)(2-hydroxybenzyl)
phosphine oxides (general procedure). Benzo-
phosphole 1, 5 g (0.025 mol), was added dropwise to a
Grignard reagent prepared by standard procedure from
0.063 mol of alkyl(aryl) bromide and 1.5 g (0.063 mol)
of Mg in 30 mL of THF. The mixture was refluxed
with stirring under argon for 2 h, let to cool to room
temperature, and hydrolyzed with a solution of
0.063 mol of H2SO4 in 30 mL of water. The aqueous
layer was extracted with CH2Cl2 (3 × 50 mL), the
solvent was removed, and the residue was washed with
diethyl ether.
1
3
2
(d) (PCH2CH2CH3, JНC = 126.2, JРС = 14.7, JHС
=
=
1
1
3.7), 29.55 br t.d (d) (PCH2, JHC = 127.66, JРС
64.3), 33.21 t.d.d (d) (C1, JHC = 127.9, JРС = 61.0,
1
1
3JНС = 4.6), 119.64 br.d.d (d) [C4(6), 1JНC = 161.4, 4JРС
=
2.3], 119.93 m (d) (C2, JРС = 8.3), 120.77 br.d.d (d)
2
[C6(4),1JHC = 161.3, JНС = 8.2, JРС = 1.7], 129.14
3
4
br.d.d.m (d) (C5, JH1C = 161.2, JНС = 8.5, JРС = 2.5),
1
3
5
131.15 d.m (d) (C7, JHC = 157.2, JРС = 6.0), 156.5 m
3
(d) (C3, JРС = 3.8). 31Р NMR spectrum (CDCl3): δP
3
Diethyl(2-hydroxybenzyl)phosphine oxide (2a).
Yield 54%, mp 114–116°С. IR spectrum (KBr), ν, cm–1:
438, 450, 467, 498, 537, 627, 693, 732, 747, 763, 801,
832, 862, 942, 974, 996, 1038, 1085, 1108, 1158,
1176, 1248, 1280, 1308, 1377, 1457, 1506, 1594,
54.8 ppm. Found, %: C 65.17; H 8.39; P 12.56.
C13H21O2P. Calculated, %: C 64.98; H 8.81; P 12.89.
Dibutyl(2-hydroxybenzyl)phosphine oxide (2c).
Yield 53 %. IR spectrum, ν, cm–1: 453, 496, 535, 553,
598, 618, 721, 754, 807, 832, 866, 902, 938, 969, 1043,
1094, 1129, 1175, 1231, 1251, 1275, 1308, 1381, 1402,
1458, 1485, 1505, 1598, 2624, 2736, 2871, 2932,
1
2595, 2707, 2921, 3461. Н NMR spectrum (CDCl3),
3
δ, ppm (J, Hz): 1.16 d.t (6H, PCH2CH3, JРН = 16.7,
3JHН = 7.7), 1.73–1.86 m (4H, PCH2, AB part of the
2
АВХ system), 3.15 d (2H, H1, JPН = 12.3), 6.85
1
2958, 3068. Н NMR spectrum (CDCl3), δ, ppm (J,
d.d.d.d (1H, H6, 3JHН = 7.5, 3JHН = 7.4, 4JHН = 1.3, 5JPН
=
=
Hz): 0.92 t [6H, P(CH2)3CH3, 3JHН = 7.3], 1.37–1.46 m
[4H, P(CH2)2CH2], 1.50–1.61 m (4H, PCH2CH2),
1.72–1.79 m (4H, PCH2), 3.15 d (2H, H1, 3JРН = 11.9),
3
4
4
1.3), 7.00 d.d.d (1H, H7, JHН = 7.5, JHН = 1.8, JPН
3
4
1.7), 7.03 d.d (1Н, Н4, JHН = 8.0, JHН = 1.3), 7.20
d.d.d.d (1Н, Н5, 3JHН = 8.0, 3JHН = 7.4, 4JHН = 1.8, 6JPН
=
3
3
6.86 br.d.d (1Н, Н6, JHН = 7.4, JHН = 7.3), 6.97 br.d
1.7), 9.74 s (1Н, OH). 13C NMR spectrum (CDCl3), δC,
(1Н, Н7, 3JНН = 7.5), 7.02 d.d (1Н, Н4, 3JHН = 8.0, 4JHН
1.2), 7.19 d.d.d.d (1Н, Н5, 3JHН = 7.9, 3JHН = 7.5, 4JHН
=
=
1
ppm (J, Hz): 5.77 qd.t (d) (PCH2CH3, JHC = 129.1,
2JHC = 4.77, JРС = 4.8), 19.76 br.t.d.q (d) (PCH2CH3,
2
1.7, 6JPН = 1.6). 31Р NMR spectrum (CDCl3): δP 56.7 ppm.
Found, %: C 66.74; H 9.52; P 11.64. C15H25O2P.
Calculated, %: C 67.14; H 9.39; P 11.54.
1JНC = 126.9, 1JРС = 65.7, 2JHС = 3.6), 32.07 br.t.d.d (d)
(C1, JHC = 127.1, JРС = 60.9, JHC = 3.1), 119.47 d.d
(d) [C4(6), 1JHC = 160.4, 3JHC = 8.0, 4JPС 2.4], 119.81 m
(d) (C2, 2JРС = 8.1), 120.70 d.d (d) [C6(4), 1JHC = 161.7,
3JНС = 8.1, 4JPС 1.9], 129.06 d.d.d (d) (C5, 1JHC = 160.3,
1
1
3
(2-Hydroxybenzyl)diphenylphosphine oxide (2d).
Yield 53%, mp 153–154°С. IR spectrum (KBr), v, cm–1:
504, 559, 604, 688, 721, 742, 785, 825, 868, 938, 968,
995, 1029, 1067, 1119, 1150, 1243, 1377, 1463, 1576,
2929, 3448. 1Н NMR spectrum (DMSO-d6), δ, ppm (J,
3JНС = 8.6, JРС = 1.8), 131.15 d.m (d) (C7, JHC
=
5
1
3
3
156.6, JРС = 5.9), 156.49 m (d) (C3, JРС = 3.7). 31Р
NMR spectrum (CDCl3): δP 55.3 ppm. Found, %: C
62.29; H 8.22; P 14.77. C11H17O2P. Calculated, %: C
62.26; H 8.02; P 14.62.
2
Hz): 3.84 d (2H, H1, JРН = 13.7), 6.63 br.d.d (1H, H6,
3
3
3JНН = 7.4, JНН = 7.4), 6.73 br.d (1H, H4, JНН = 8.0),
6.98 d.d.d.d (1H, H5, 3JНН = 7.7, 3JНН = 7.6, 4JНН = 1.7,
6JPН = 1.6), 7.09 br.d (1H, H7, 3JНН = 7.7), 7.46–7.52 m
(2-Hydroxybenzyl)dipropylphosphine oxide (2b).
Yield 63%, mp 72°С. IR spectrum (KBr), ν, cm–1: 449,
467, 494, 535, 554, 601, 619, 730, 755, 793, 842, 869,
(4Н, Нm), 7.53–7.57 m (2Н, Нp), 7.79 m (4Н, Нo, 3JРН
=
11.4), 9.66 s (OH, 1Н). 31Р NMR spectrum (DMSO-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 3 2016

2-ETHOXY-2,3-DIHYDRO[d][1,2]OXAPHOSPHOLE 2-OXIDE
533
Chem., 2015, vol. 460, no. 2, p. 57. DOI: 10.1134/
S001250081502007X.
d6): δP 39.0 ppm. Found, %: C 74.11; H 5.88; P 9.77.
C19H17O2P. Calculated, %: C 74.03; H 5.52; P 10.06.
14. Matveeva, A.G., Tu, A.M., Safiulina, A.M., Bodrin, G.V.,
Goryunov, E.I., Goryunova, I.B., Sinegribova, O.A.,
and Nifantiev, E.E., Russ. Chem. Bull., 2013, vol. 62,
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15. Zairov, R.R., Tatarinov, D.A., Shamsutdinova, N.A.,
Mustafina, A.R., Rizvanov, I.Kh., Syakaev, V.V.,
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ACKNOWLEDGMENTS
The work was financially supported by the Russian
Foundation for Basic Research (project no. 16-03-
00451).
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