Novel synthesis of stable 1,5-diionic organophosphorus compounds from the reaction between triphenylphosphine and acetylenedicarboxylic acid in the presence of N-H heterocyclic compounds

Article abstract of DOI:10.1007/s00706-012-0743-3

The addition of triphenylphosphine to acetylenedicarboxylic acid in the presence of N-H heterocyclic compounds such as carbazole, 2-indolinone, 2-benzoxazolinone, 2-mercaptobenzoxazole, 2,4-thiazolidinedione, benzimidazole, isatin, or saccharin leads to s

Full text of DOI:10.1007/s00706-012-0743-3

Monatsh Chem (2012) 143:1681–1685
DOI 10.1007/s00706-012-0743-3
ORIGINAL PAPER
Novel synthesis of stable 1,5-diionic organophosphorus
compounds from the reaction between triphenylphosphine
and acetylenedicarboxylic acid in the presence of N–H
heterocyclic compounds
•
Morteza Ziyaadini Malek Taher Maghsoodlou
•
•
Nourallah Hazeri Sayyed Mostafa Habibi-Khorassani
Received: 1 June 2011 / Accepted: 26 February 2012 / Published online: 18 April 2012
Ó Springer-Verlag 2012
Abstract The addition of triphenylphosphine to acety-
lenedicarboxylic acid in the presence of N–H heterocyclic
compounds such as carbazole, 2-indolinone, 2-benzoxazo-
linone, 2-mercaptobenzoxazole, 2,4-thiazolidinedione,
benzimidazole, isatin, or saccharin leads to stable 1,5-diionic
organophosphorus compounds in excellent yields at ambient
temperature.
phosphorus compounds as elusive transient species [8–10].
In all of these reactions in which this diionic system is
postulated, the betaine cannot be isolated but appears to
occur as an intermediate on the pathway to an observed
product. Researchers have recently described the synthesis
of stable diionic compounds from the reaction between
triphenylphosphine and electron-deficient acetylenic esters
in the presence of CH acids [11–14]. In continuation of our
investigation of the reaction between trivalent phosphorus
nucleophiles and acetylenic esters in the presence of organic
compounds containing NH, OH, or SH groups [16–28], we
wish to report a novel and facile one-pot, three-component
reaction between triphenylphosphine (1), acetylenedicarb-
oxylic acid (ADA, 2), and N–H heterocyclic compounds
3a–3h for the preparation of the crystalline and stable 1,5-
diionic organophosphorus compounds 4a–4h in excellent
yields at ambient temperature (Scheme 1).
Keywords Acetylenedicarboxylic acid Á
Triphenylphosphine Á 1,5-Diionic organophosphorus
compounds Á N–H heterocyclic compounds Á
Decarboxylation
Introduction
Trivalent phosphorus compounds are known to be nucleo-
philes, whereas they behave as electron donors toward good
electron acceptors either in the ground or excited state
[1, 2]. In recent years there has been increasing interest in
the synthesis of organophosphorus compounds, i.e., those
bearing a carbon atom bound directly to a phosphorus atom
[3–15]. This interest has resulted from the recognition of the
value of such compounds in a variety of biological, indus-
trial, and chemical synthetic uses [3–5]. A number of
reactions have been observed which involve 1,4-diionic
Results and discussion
The decarboxylation of carboxylic acids under the influ-
ence of the electron-withdrawing triphenylphosphonium
group at the a-position has been recently described
[29, 30]. In the present three-component reaction, 1,5-di-
ionic organophosphorus compounds are generated via
decarboxylation of an intermediate ylide as a key step in
the reaction. On the basis of the well-established chemistry
of trivalent phosphorus nucleophiles, it is reasonable to
assume that compounds 4a–4h result from the initial
addition of triphenylphosphine to acetylenedicarboxylic
acid and subsequent protonation of the 1:1 adduct 5 by
proton source 3 to form 6. Then the positively charged ion
6 is attacked by the anion of the NH acid to generate
phosphorus ylide 7. Ylide 7 is converted to compound 8
M. T. Maghsoodlou (&) Á N. Hazeri Á S. M. Habibi-Khorassani
Department of Chemistry, Faculty of Science,
University of Sistan and Baluchestan,
P.O. Box 98135-674, Zahedan, Iran
e-mail: mt_maghsoodlou@yahoo.com
M. Ziyaadini
Faculty of Marine Science, Chabahar Maritime University,
Chabahar, Iran
123

1682
M. Ziyaadini et al.
2
2
Z
P
group at d = 3.80 ppm with JHH = 16.1 Hz, JHP
=
O
C
O
C
H
H
COO
H
10.3 Hz, 3JHH = 10.4 Hz, and d = 4.76 ppm with
CH2Cl2
r.t., 24h
Ph3P
HO
C
C
OH
Z-H
+
+
2JHH = 16.1 Hz, JHP = 13.1 Hz, JHH = 3.0 Hz as two
sets of treble doublets. The signal at d = 5.22 ppm corre-
sponds to the methine proton which appears as treble
2
3
Ph
1
2
3
Ph
Ph
4
doublets with 3JHP = 13.1 Hz, 3JHH = 10.4 Hz, and 3JHP
=
Yield/%
91
3 4
,
3 4
Z
,
Z
Yield/%
94
10.3 Hz (Fig. 1). The H-decoupled 13C NMR spectrum of
4a showed two characteristic doublets at d = 24.42
(1JCP = 53.8 Hz) and 51.67 ppm (2JCP = 5.6 Hz) for
CH2–P (methylene group) and CH–CP (methine group)
moieties, respectively. The 13C NMR spectra are in
agreement with the structure of 4a. Partial assignments of
these resonances are given in the ‘‘Experimental’’ section.
Furthermore, DEPT spectra of 4a indicated two chemical
shifts for the methylene carbon and methine carbon at d =
24.4 and 51.6 ppm, respectively. The 31P NMR spectra of
compound 4a displayed a signal at d = 20.44 ppm which
is consistent with the presence of a (Ph)3P?–C grouping
[31, 32]. The mass spectrum of 4a displayed the molecular
ion peak at m/z = 499.
1
O
O
e
f
a
b
N
N
O
S
O
N
93
O
O
86
N
O
N
N
O
N
c
d
91
90
g
h
87
89
S
O
S
O
O
N
N
Scheme 1
In summary, the present synthesis of 1,5-diionic orga-
nophosphorus compounds offers significant advantages for
the synthesis of betaines which are a new category of
organophosphorous compounds: not only is the reaction
performed under neutral conditions, but also substances
can be mixed without any activation or modification.
and subsequently to intermediate 9 in a process of
H-transfer and elimination of CO2. Ylide 9 can be con-
verted to desired product 4 by another H-transfer (see
speculative proposed mechanism in Scheme 2). No product
other than 4 could be detected by NMR spectroscopy. The
structures of compounds 4a–4h were deduced from the
elemental analyses, IR, 1H, 13C, 31P NMR, and mass
Experimental
1
spectra. A plausible interpretation of the H spectral data
for compound 4a is that the signal at d = 5.22 ppm cor-
responds to the methine proton with JHP coupling constant
13.1 Hz, whereas signals at 4.76 and 3.80 ppm correspond
to the diastereotopic protons of the methylene group, with
JHP coupling constants 13.1 and 10.3 Hz, respectively.
Vicinal coupling constants are equal to 3.0 and 10.4 Hz,
respectively, and the geminal coupling constant -16.1 Hz.
Melting points and IR spectra of all compounds were mea-
sured on an Electrothermal 9100 apparatus and a JASCO
1
FT-IR spectrometer, respectively. H and 13C NMR spectra
were recorded on Bruker 500 or 400 MHz instruments using
CDCl3 as a solvent and TMS as internal standard (500.1 or
400.2 MHz and 125.8 or 100.6 MHz, respectively). Ele-
mental analyses for C, H, and N were performed using a
Heraeus CHN-O-Rapid analyzer. In addition, the mass
spectra were recorded on a Shimadzu GCMS-QP5050A
1
The H NMR spectra of compound 4a exhibited two
signals for the diastereotopic protons of the methylene
Scheme 2
O
C
O
C
Z
CO2H
C
Z-H
3
CO2H
HO2C
Ph3P
HO2C
Ph3P
HO
C
C
OH
C
H
CO2H
CO2H
C
C
H
Ph3P
2
Z
Ph3P
5
6
7
1
H-transfer
Z
Z
Z
H
H
COO
H
H
H
CO2H
PPh3
H-transfer
H
CO2H
CO2
- CO2
H
P
Ph
Ph
Ph
PPh3
4
9
8
123

Novel synthesis of stable 1,5-diionic organophosphorus compounds
1683
2JHH = 22.1 Hz, CH2 of C8H7NO), 3.66 (1H, ddd,
2
3
2JHH = 16.5 Hz, JHP = 10.0 Hz, JHH = 9.7 Hz, CH2–P),
4.70 (1H, ddd, 2JHH = 16.2 Hz, 2JHP = 13.7 Hz,
3JHH = 3.3 Hz, CH2–P), 5.36 (1H, ddd, JHP = 13.6 Hz,
3
3JHH = 9.2 Hz, JHH = 3.3 Hz, CH–CP), 6.89–7.81 (19H,
3
m, CHarom
)
ppm; 13C NMR (CDCl3, 100.6 MHz):
1
d = 23.22 (d, JCP = 52.3 Hz, CH–P), 35.16 (s, CH2 of
C8H7NO), 49.03 (d, JCP = 5.0 Hz, CH2–CP), 110.08,
117.46, 118.36, 122.43, 142.35, 175.05 (s, 7C of C8H7NO),
1
118.38 (d, JCP = 86.5 Hz, Cipso), 130.21 (d, JCP
2
13.1 Hz, Cmeta), 133.51 (d, JCP = 10.5 Hz, Cortho),
2
3
=
4
3
134.87 (d, JCP = 3.0 Hz, Cpara), 168.09 (d, JCP = 12.0
Hz, C=O acid) ppm; 31P NMR (CDCl3, 162.0 MHz):
d = 21.01 (Ph3P?–C) ppm; IR (KBr): m = 1,700 (C=O
heterocyclic), 1,614 and 1,438 (COO asym and sym) cm-1
;
MS: m/z (%) = 463 (M?, 1), 277 (Ph3PCH3, 2), 262 (Ph3P,
100), 183 (PPh2, 41), 133 (C8H7NO, 2), 108 (PPh, 17), 77
(Ph, 4), 44 (CO2, 8).
1
Fig. 1 Part of the H NMR spectrum of compound 4a
2-(2-Oxobenzo[d]oxazol-3(2H)-yl)-3-(triphenylphospho-
nio)propanoate (4c, C28H22NO4P)
mass spectrometer operating at an ionization potential of
70 eV. Triphenylphosphine, acetylenedicarboxylic acid, and
N–H acid derivatives were purchased from Fuka, Merck, and
Acros and used without further purification.
1
Light yellow powder; yield 87%; m.p.: 103–106 °C; H
3
NMR (CDCl3, 400.2 MHz): d = 3.87 (1H, ddd, JHH
15.9 Hz, JHP = 10.3 Hz, JHH = 10.4 Hz, CH2–P), 4.81
=
2
3
2
(1H, ddd, JHH = 16.1 Hz, JHP = 13.1 Hz, JHH = 3.0
2
3
2-(9H-Carbazol-9-yl)-3-(triphenylphosphonio)propanoate
(4a, C33H26NO2P)
3
Hz, CH2–P), 5.18 (1H, ddd, JHP = 13.3 Hz, JHH
3
=
3
To a magnetically stirred solution of triphenylphosphine
(1 mmol) and NH acid 3a (1 mmol) in 10 cm3 CH2Cl2 was
added dropwise a mixture of acetylenedicarboxylic acid
(1 mmol) in 1 cm3 Et2O over 10 min at ambient tempera-
ture. After 24 h stirring at ambient temperature the solvent
was removed and the residue was crystallized from diethyl
ether to yield 4a as a light yellow powder. Yield 91%; m.p.:
10.3 Hz, JHH = 3.0 Hz, CH–CP), 7.45–7.80 (19H, m,
CHarom) ppm; 13C NMR (CDCl3, 100.6 MHz): d = 24.04
(d, JCP = 53.3 Hz, CH–P), 51.78 (d, JCP = 6.0 Hz,
1
2
CH2–CP), 109.54, 110.71, 122.34, 124.05, 142.25,
1
154.09, 159.95 (s, 7C of C7H4NO2), 118.12 (d, JCP
=
3
86.6 Hz, Cipso), 130.23 (d, JCP = 13.1 Hz, Cmeta), 133.36
2
(d, JCP = 10.1 Hz, Cortho), 134.91 (d, JCP = 3.0 Hz,
4
1
3
para), 167.25 (d, JCP = 12.1 Hz, C=O acid) ppm; 31P
84–87 °C; H NMR (CDCl3, 500.1 MHz): d = 3.80 (1H,
ddd, JHH = 16.1 Hz, JHH = 10.4 Hz, JHP = 10.3 Hz,
C
2
3
2
NMR (CDCl3, 162.0 MHz): d = 20.30 (Ph3P?–C) ppm;
IR (KBr): m = 1,761 (C=O heterocyclic), 1,638 and 1,438
(COO asym and sym) cm-1; MS: m/z (%) = 467 (M?, 1),
277 (Ph3PCH3, 8), 262 (Ph3P, 100), 183 (PPh2, 68), 135
(C7H5NO2, 3), 108 (PPh, 13), 77 (Ph, 3), 44 (CO2, 6).
2
2
CH2–P), 4.76 (1H, ddd, JHH = 16.1 Hz, JHP = 13.1
3
Hz, JHH = 3.0 Hz, CH2–P), 5.22 (1H, ddd, JHP
3
=
13.1 Hz, 3JHH = 10.4 Hz, 3JHH = 3.0 Hz, CH–CP),
7.00–7.84 (23H, m, CHarom) ppm; 13C NMR (CDCl3,
1
125.7 MHz): d = 24.42 (d, JCP = 53.8 Hz, CH2–P),
2-(2-Thioxobenzo[d]oxazol-3(2H)-yl)-3-(triphenylphos-
phonio)propanoate (4d, C28H22NO3PS)
51.67 (d, 2JCP = 5.6 Hz, CH–CP), 109.65, 110.54, 122.45,
124.05, 142.32, 154.04 (s, 12C of C12H8N), 118.11 (d,
1JCP = 86.9 Hz, Cipso), 130.26 (d, 3JCP = 12.7 Hz, Cmeta),
Cream powder; yield 89%; m.p.: 97–100 °C; 1H NMR
(CDCl3, 500.1 MHz): d = 3.67 (1H, ddd, 2JHH = 15.7 Hz,
2
4
133.32 (d, JCP = 10.0 Hz, Cortho), 134.97 (d, JCP = 2.8
Hz, Cpara), 166.94 (d, 3JCP = 11.6 Hz, C=O acid) ppm; 31
NMR (CDCl3, 202.4 MHz): d = 20.44 (Ph3P?–C) ppm; IR
3
2JHP = 8.5 Hz, JHH = 8.4 Hz, CH2–P), 4.65 (1H, ddd,
P
2
3
2JHH = 15.1 Hz, JHP = 13.8 Hz, JHH = 6.0 Hz, CH2–P),
5.87 (1H, ddd, 3JHP = 13.5 Hz, 3JHH = 8.2 Hz,
(KBr): m = 1,639 and 1,438 (COO asym and sym) cm-1
;
3JHH = 6.0 Hz, CH–CP), 7.47–7.81 (19H, m, CHarom
)
MS: m/z (%) = 499 (M?, 1), 277 (Ph3PCH3, 15), 262 (Ph3P,
100), 183 (PPh2, 69), 108 (PPh, 25), 77 (Ph, 8), 44 (CO2, 5).
ppm; 13C NMR (CDCl3, 125.7 MHz): d = 25.43 (d,
1JCP = 56.5 Hz, CH–P), 56.06 (d, JCP = 3.1 Hz, CH2–
CP), 109.98, 122.34, 124.05, 134.57, 146.75, 156.14 (s, 6C
2
2-(2,3-Dihydro-2-oxo-1H-indol-1-yl)-3-(triphenylphosphonio)-
propanoate (4b, C29H22NO3P)
1
of C7H4NOS), 118.54 (d, JCP = 88.0 Hz, Cipso), 130.02
1
3
(d, JCP = 12.7 Hz, Cmeta), 133.43 (d, JCP = 9.9 Hz,
2
Light brown powder; yield 86%; m.p.: 123–125 °C; H
4
ortho), 135.52 (d, JCP = 2.6 Hz, Cpara), 166.58 (d,
NMR (CDCl3, 400.2 MHz): d = 2.56, 3.16 (2H, d,
C
123

1684
M. Ziyaadini et al.
2
3JCP = 8.2 Hz, C=O acid), 180.26 (C=S) ppm; 31P NMR
(CDCl3, 202.4 MHz): d = 20.20 (Ph3P?–C) ppm; IR
(KBr): m = 1,647 and 1,400 (COO asym and sym), 1,470
(C=S) cm-1; MS: m/z (%) = 483 (M?, 1), 277 (Ph3PCH3,
9), 262 (Ph3P, 100), 183 (PPh2, 80), 151 (C7H5NOS, 17),
108 (PPh, 26), 77 (Ph, 10), 44 (CO2, 5).
3JHH = 9.1 Hz, JHP = 9.2 Hz, CH2–P), 4.87 (1H, ddd,
2JHH = 16.3 Hz, JHP = 13.1 Hz, JHH = 4.0 Hz, CH2–
2
3
3
3
P), 5.30 (1H, ddd, JHP = 13.4 Hz, JHH = 8.6 Hz,
3JHH = 4.1 Hz, CH–CP), 7.34–7.81 (19H, m, CHarom),
7.95 (1H, s, CH=N) ppm; 13C NMR (CDCl3, 100.6 MHz):
1
d = 27.21 (d, JCP = 53.3 Hz, CH–P), 54.98 (d,
2JCP = 5.0 Hz, CH2–CP), 110.46, 119.91, 122.08,
122.90, 128.44, 133.78, 143.21 (s, 7C of C7H5N2),
2-(2,3-Dihydro-2,3-dioxo-1H-indol-1-yl)-3-(triphenylphos-
phonio)propanoate (4e, C29H22NO4P)
1
118.50 (d, JCP = 87.6 Hz, Cipso), 130.18 (d, JCP
2
13.1 Hz, Cmeta), 133.19 (d, JCP = 10.6 Hz, Cortho),
3
=
1
Orange powder; yield 94%; m.p.: 148–151 °C; H NMR
(CDCl3, 400.2 MHz): d = 3.69 (1H, ddd, 2JHH = 16.1 Hz,
4
3
134.70 (d, JCP = 3.1 Hz, Cpara), 168.83 (d, JCP = 10.1
Hz, C=O acid) ppm; 31P NMR (CDCl3, 162.0 MHz):
d = 20.87 (Ph3P?–C) ppm; IR (KBr): m = 1,639 and 1,400
(COO asym and sym) cm-1; MS: m/z (%) = 450 (M?, 1),
277 (Ph3PCH3, 6), 262 (Ph3P, 100), 183 (PPh2, 80), 132
(C8H9N2, 5), 108 (PPh, 26), 77 (Ph, 9), 44 (CO2, 2).
3
2JHP = 10.3 Hz, JHH = 10.4 Hz, CH2–P), 4.82 (1H, ddd,
2
3
2JHH = 16.7 Hz, JHP = 12.9 Hz, JHH = 2.4 Hz, CH2–
3
P), 5.32 (1H, ddd, JHP = 13.4 Hz, JHH = 11.0 Hz,
3
3JHH = 2.4 Hz, CH–CP), 7.05–7.84 (19H, m, CHarom
)
ppm; 13C NMR (CDCl3, 100.6 MHz): d = 23.90 (d,
1JCP = 53.3 Hz, CH–P), 49.52 (d, JCP = 6.0 Hz, CH2–
CP), 112.67, 117.87, 123.77, 124.95, 138.54, 149.23,
2
2-(2,4-Dioxothiazolidin-3-yl)-3-(triphenylphosphonio)-
propanoate (4h, C24H20NO4PS)
Light yellow powder; yield 90%; m.p.: 94–97 °C; 1H NMR
1
157.96, 182.33 (s, 8C of C8H4NO2), 118.11 (d, JCP
=
3
86.5 Hz, Cipso), 130.40 (d, JCP = 13.1 Hz, Cmeta), 133.55
2
(d, JCP = 10.0 Hz, Cortho), 135.21 (d, JCP = 2.0 Hz,
4
2
(CDCl3, 500.1 MHz): d = 3.58, 3.74 (2H, d, JHH = 17.1
Hz, CH2 heterocyclic), 3.88 (1H, ddd, JHH = 16.0 Hz,
3
2
C
para), 166.67 (d, JCP = 11.1 Hz, C=O acid) ppm; 31P
2
NMR (CDCl3, 162.0 MHz): d = 20.82 (Ph3P?–C) ppm; IR
(KBr): m = 1,735 and 1,650 (C=O heterocyclic), 1,610 and
1,438 (COO asym and sym) cm-1; MS: m/z (%) = 479
(M?, 1), 333 (M - C8H4NO2, 1), 277 (Ph3PCH3, 10), 262
(Ph3P, 100), 183 (PPh2, 64), 108 (PPh, 21), 77 (Ph, 17), 44
(CO2, 13).
3JHH = 9.5 Hz, JHP = 9.4 Hz, CH2–P), 4.76 (1H, ddd,
2JHH = 16.1 Hz, JHP = 14.1 Hz, JHH = 4.0 Hz, CH2–
2
3
3
P), 5.02 (1H, ddd, JHP = 14.0 Hz, JHH = 9.1 Hz,
3
3JHH = 4.0 Hz, CH–CP), 7.28–7.82 (15H, m, CHarom
)
ppm; 13C NMR (CDCl3, 125.7 MHz): d = 22.93 (d,
1JCP = 55.6 Hz, CH–P), 33.44 (s, CH2 heterocyclic),
2
51.28 (d, JCP = 5.1 Hz, CH2–CP), 119.10 (d, JCP
1
=
2-(1,1-Dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)-3-(tri-
phenylphosphonio)propanoate (4f, C28H22NO5PS)
3
87.2 Hz, Cipso), 130.33 (d, JCP = 12.7 Hz, Cmeta), 133.27
2
(d, JCP = 9.8 Hz, Cortho), 134.89 (d, JCP = 2.3 Hz,
4
White powder; yield 93%; m.p.: 94–98 °C; 1H NMR
3
C
para), 166.61 (d, JCP = 10.5 Hz, C=O acid), 171.38,
(CDCl3, 500.1 MHz): d = 3.88 (1H, ddd, 2JHH = 17.3 Hz,
172.00 (s, 2C=O heterocyclic) ppm; 31P NMR (CDCl3,
202.4 MHz): d = 19.09 (Ph3P?–C) ppm; IR (KBr):
m = 1,749 and 1,678 (C=O heterocyclic), 1,610 and 1,438
(COO asym and sym) cm-1; MS: m/z (%) = 449 (M?, 1),
277 (Ph3PCH3, 12), 262 (Ph3P, 100), 183 (PPh2, 84), 115
(C3H3NO2S, 9), 108 (PPh, 71), 77 (Ph, 12), 44 (CO2, 20).
2
3JHH = 9.5 Hz, JHP = 9.4 Hz, CH2–P), 4.69 (1H, ddd,
2
3
2JHH = 16.8 Hz, JHP = 13.2 Hz, JHH = 6.9 Hz, CH2–
3
P), 4.85 (1H, ddd, JHP = 13.5 Hz, JHH = 8.9 Hz,
3
3JHH = 6.7 Hz, CH–CP), 7.53–7.95 (19H, m, CHarom
)
ppm; 13C NMR (CDCl3, 125.7 MHz): d = 24.79 (d,
1JCP = 49.1 Hz, CH–P), 49.99 (d, JCP = 4.1 Hz, CH2–
CP), 116.33, 117.06, 119.73, 123.42, 131.52, 131.82,
2
Acknowledgments We gratefully acknowledge the financial sup-
port from the Research Council of University of Sistan and
Baluchestan.
1
168.85 (s, 7C of C7H4NO3S), 118.60 (d, JCP = 83.4 Hz,
C
ipso), 130.65 (d, 3JCP = 13.2 Hz, Cmeta), 133.85 (d, 2JCP
=
4
10.6 Hz, Cortho), 135.68 (d, JCP = 2.7 Hz, Cpara), 166.71
(d, JCP = 10.1 Hz, C=O acid) ppm; 31P NMR (CDCl3,
3
202.4 MHz): d = 18.95 (Ph3P?–C) ppm; IR (KBr):
m = 1,728 (C=O heterocyclic), 1,638 and 1,438 (COO
asym and sym), 1,338 (SO2) cm-1; MS: m/z (%) = 515
(M?, 1), 277 (Ph3PCH3, 7), 262 (Ph3P, 100), 183 (PPh2, 74),
108 (PPh, 30), 77 (Ph, 6), 44 (CO2, 18).
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Cream powder; yield 91%; m.p.: 90–92 °C; 1H NMR
(CDCl3, 400.2 MHz): d = 4.03 (1H, ddd, 2JHH = 15.8 Hz,
123

Novel synthesis of stable 1,5-diionic organophosphorus compounds
1685
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