A new route to mercury-containing triphenylphosphonium salts with electron-withdrawing groups at the P atom and some transformations of these compounds

Article abstract of DOI:10.1023/B:RUGC.0000031851.88852.ce

(Aroylmethyl)triphenylphosphonium salts react with mercury(II) trifluoroacetate with replacement of the labile methylene hydrogen atom by the HgOCOCF₃ group to give mercury-containing triphenylphosphonium salts in quantitative yields. Treatment of the mercurated salts with potassium carbonate yields mercury-containing triphenylphosphonium ylides of symmetrical and unsymmetrical structures, which enter Wittig reaction with aromatic aldehydes to form the corresponding mercurated olefins (Z isomers) and triphenylphosphine oxide.

Full text of DOI:10.1023/B:RUGC.0000031851.88852.ce

Russian Journal of General Chemistry, Vol. 74, No. 4, 2004, pp. 530 535. Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 4, 2004,
pp. 581 586.
Original Russian Text Copyright
2004 by Nevstruev, Moskalenko, Boev, and Porokhnya.
A New Route to Mercury-Containing Triphenylphosphonium
Salts with Electron-Withdrawing Groups at the P Atom
and Some Transformations of These Compounds
A. N. Nevstruev, A. I. Moskalenko, V. I. Boev, and S. N. Porokhnya
Lipetsk State Pedagogical University, Lipetsk, Russia
Received April 17, 2002
Abstract (Aroylmethyl)triphenylphosphonium salts react with mercury(II) trifluoroacetate with replace-
ment of the labile methylene hydrogen atom by the HgOCOCF3 group to give mercury-containing tri-
phenylphosphonium salts in quantitative yields. Treatment of the mercurated salts with potassium carbonate
yields mercury-containing triphenylphosphonium ylides of symmetrical and unsymmetrical structures, which
enter Wittig reaction with aromatic aldehydes to form the corresponding mercurated olefins (Z isomers) and
triphenylphosphine oxide.
Mercury-containing triphenylphosphonium salts
prepared for the first time more than 40 years ago [1]
attract researchers’ attention thanks to their potential
in organic synthesis [2]. These compounds were pre-
pared by addition of mercury salts to stable [3 7] and
unstable [1, 8] triphenylphosphorylides; in the latter
case, however, difficult-to-separate mixtures of prod-
ucts were obtained.
the reaction mixture with NaBr or NaClO4) by addi-
tion of mercury(II) trifluoroacetate to the correspond-
ing aroyltriphenylphosphorylides [12] at room temper-
ature in ethanol.
Ph3P=CHC(O)Ar + Hg(OCOCF3)2
+
NaX
EtOH
[Ph3PCHC(O)Ar] OCOCF3
V VIII
CF3COONa
HgOCOCF3
In this work, proceeding with studies on mercura-
tion of onium compounds containing fairly labile
hydrogen atoms [9], we performed for the first time
the similar reactions with a number of accessible and
stable triphenylphosphonium salts [10, 11]. We found
that refluxing of equimolar amounts of mercury(II)
trifluoroacetate and (aroylmethyl)triphenylphoshoni-
um salts I IV in anhydrous ethanol results in smooth
mercuration of I IV with replacement of the methyl-
ene hydrogen atom by the HgOCOCF3 group. The
reactions afford mercury-containing triphenylphospho-
nium salts V VIII in quantitative yields (Table 1) and
ethyl trifluoroacetate in 70 80% yield (GLC data).
This fact suggests that mercuration of I IV on
heating in ethanol occurs via initial formation of phos-
phorylides, followed by addition of mercury(II) tri-
fluoroacetate. The first step is apparently limiting, and
the second step is fast.
Salts V VIII are colorless or weakly colored solids
melting with decomposition; they are readily soluble
in polar organic solvents, poorly soluble in water, and
insoluble in hydrocarbons and diethyl ether. Their
composition and structure are confirmed by elemental
1
analysis (Table 1), H NMR and IR spectra (Table 2),
and chemical transformations.
+
[Ph3PCH2C(O)Ar]X + Hg(OCOCF3)2
The presence of the covalent C Hg bond in V VIII
I IV
is proved by coupling between the methine proton and
EtOH
+
1
199Hg nucleus, observed in the H NMR spectrum,
[Ph3PCHC(O)Ar]X ,
CF3COOEt,
H2O
and also by a downfield shift of the methine proton
signal due to magnetic anisotropy produced by the
mercury-containing substituent [13].
HgOCOCF3
V VIII
Ar = Ph (I, V), 4-BrC6H4 (II, IV, VI, VIII), 4-NO2C6H4
(III, VII); X = Br (I III, V VII), ClO4 (IV, VIII).
The chemical properties of V VIII are consistent
with their structure. On heating in HCl, they decom-
pose to give the starting salts I IV and Hg2+ ions,
which are quantitatively precipitated in the form of
The same salts were obtained (after treatment of
1070-3632/04/7404-0530 2004 MAIK Nauka/Interperiodica

A NEW ROUTE TO MERCURY-CONTAINING TRIPHENYLPHOSPHONIUM SALTS
531
Table 1. Reaction times, yields, constants, and analytical data for V VIII, X XV, and XVII XXVII
Decom-
position
Found, %
Calculated, %
Comp.
no.
Reaction
time, min
Yield,
%
Formula
point,
C
Hg
N (Br)
Hg
N (Br)
V
VI
VII
60
60
60
35
15
10
10
30
30
10
60
60
90
90
80
98
99
99
98
79
77
76
68
65
90
73
71
70
30
50
58
71
46
59
64
56
105 107
108 110
100 102
138 140
151 152
149 150
162 163
164 165
168 170
135 136
139 140
165 166
184 186
175 176
181 182
173 174
166 168
193 195
185 188
192 194
201 203
25.74
23.41
23.59
22.63
29.08
26.82
27.56
19.93
18.00
18.73
33.08
30.85
32.18
31.64
31.96
35.28
32.73
34.31
32.83
33.84
23.35
(10.28)
(18.53)
C28H21BrF3HgO3P
C28H20Br2F3HgO3P
25.93
23.53
24.51
23.00
28.96
26.00
27.20
20.93
17.97
19.71
33.46
31.12
32.59
31.27
32.12
35.47
32.85
34.49
33.02
33.97
23.26
(10.34)
(18.77)
1.90 (9.68) C28H20BrF3HgNO5P
1.7
(9.77)
VIII
(13.08)a
C28H20BrClF3HgO7P
C28H20F3HgO3P
C28H19BrF3HgO3P
C28H19F3HgNO5P
C52H40HgO2P2
C52H38Br2HgO2P2
C52H38HgN2O6P2
C17H10BrF3HgO3
(13.25)a
Xb
XI
(10.63)
1.78
(10.37)
1.90
XII
XIIIc
XIV
XV
(14.51)
3.00
(13.22)
(14.33)
2.75
XVII
XVIII
XIX
XX
XXI
XXII
XXIII
XXIV
XXV
XXVI
XXVII
(13.34)
2.17 (12.41)
(13.00)
(12.47)
(12.81)
2.48
2.31 (12.36) C17H9BrF3HgNO5
(12.75)
(12.23)
(12.64)
2.36
4.42
2.43
C17H10BrF3HgO4
C19H12BrF3HgO4
C19H11BrF3HgO3
C17H10F3HgNO5
C17H9F3HgN2O7
C17H10F3HgNO6
C19H12F3HgNO6
C19H11F3HgNO5
120
60
120
100
100
30
4.59
2.41
2.30
2.37
2.45
2.41
3.18 (18.26) C30H18Br2HgN2O6
3.25 (18.55)
a
b
c
Br + Cl.
Found P, %: 13.08. Calculated P, %: 13.25.
Found P, %: 6.54. Calculated P, %: 6.47.
HgS on passing H2S through the reaction mixture
after decomposition. On treatment of salt V with NaCl
in aqueous alcohol on heating, it quantitatively trans-
formed into known [4] chloride IX identified by the
melting point and IR spectrum.
tained the same symmetrical mercury-containing
ylides XIII XV by reactions of X XII with ammonia
in chloroform. Ammonia is known [14] to be a versa-
tile symmetrizing agent for many organomercury
salts.
It should also be noted that treatment of IX with
potassium carbonate in DMF yields the known [3, 4]
phosphorylide XVI, whereas in acetonitrile the sym-
metrical ylide XIII is formed, i.e., the pattern was
similar to that noted above.
NaCl
+
V
[Ph3PCHC(O)Ar]Cl
NaBr,
F3CCOONa
HgCl
IX
+
DMF
Ph3PCC(O)Ar
We believe that formation of mercurated phosphor-
ylides X XV on treatment of V VIII with aqueous
sodium carbonate is a convincing chemical evidence
of the covalent nature of the C Hg bond in these com-
pounds. The structure of the ylides formed significant-
ly depended on the solvent in which the reaction was
performed and also on the anion X (e.g., in VI and
VIII). If the reaction was performed in dimethylform-
amide (DMF), bromides V VII transformed into
ylides X XII, whereas in acetonitrile only symmetri-
cal ylides XIII XV were obtained. Treatment of per-
chlorate VIII with aqueous K2CO3 gave symmetrical
ylide XIV only, irrespective of the solvent. We ob-
HgOCOCF3
X XII
K2CO3
V VII
KBr,
CO2,
H2O
NH3, CHCl3
+
+
CH3CN
Ph3PC Hg CPPh3
OCAr OCAr
XIII XV
K2CO3
VIII
KClO4, CO2, H2O
Ar = Ph (X, XIII), 4-BrC6H4 (XI, XIV), 4-NO2C6H4
(XII, XV).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 4 2004

532
NEVSTRUEV et al.
Table 2. IR and 1H NMR data for V VIII, X XV, and XVII XXVII
1
IR spectrum, , cm
1H NMR spectrum, , ppm
P(C6H5)3, m
Comp.
no.
aromatic
system
C Br
(NO2)
CH
C O
C=O
C=C
Ar CO
2(3)
(
J
, Hz)
or R
HgH
V
1602, 1587,
1501, 1473
1598, 1582,
1496, 1468
1600, 1589,
1506, 1463
1598, 1583,
1496, 1463
1605, 1578,
1508, 1463
1603, 1581,
1503, 1462
1606, 1587,
1510, 1471
1607, 1592,
1508, 1463
1605, 1582,
1504, 1471
1608, 1591,
1512, 1475
1545, 1500,
1440
1221 1672, 1620
1218 1678, 1622
1220 1680, 1638
1218 1679, 1622
1231 1660, 1562
1228 1662, 1560
1225 1668, 1572
1568
6.62 m (272)
6.66 m (275)
6.71 m (283)
6.65 m (276)
8.91 8.05
8.92 8.08
8.96 8.12
8.94 8.10
8.78 8.02
8.80 8.02
8.90 8.04
8.62 7.97
8.60 7.93
8.72 8.01
7.62 7.88 m
(5H)
7.72 7.96 m
(4H)
7.83 8.05 d.d
(4H)
7.73 7.98 m
(4H)
7.50 7.72 m
(5H)
7.68 7.85 m
(4H)
7.65 7.92 d.d
(4H)
7.42 7.63 m
(5H)
VI
760
(1352)
762
VII
VIII
X
XI
760
XII
(1350)
XIII
XIV
XV
1562
761
(1348)
762
7.58 7.82 m
(4H)
7.58 7.84 d.d
(4H)
1570
XVII
XVIII
XIX
XX
1218 1672, 1625
1220 1675, 1627
1600 6.93 s (598)
8.36 8.03 m (5H) 8.92 8.76 d.d
(4H)
1546, 1498,
1445
1562, 1502,
1458
1583, 1532,
1480, 1463
760,
(1356)
762
1598 6.89 s (588) 8.38 8.12 d.d (4H) 8.94 8.78 d.d
(4H)
1602 6.90 s (602) 8.25 7.93 d.d (4H) 8.91 8.69 d.d
(4H)
1222, 1677, 1625
3560a
1256, 1678, 1632
1217
760
1598, 6.98 m (628) 6.76 m (2H), 7.58 s 8.90 8.63 d.d
1618
(1H), 6.10 5.87 m
(4H)
(4H)
XXI
1546, 1502,
1448
1558, 1499,
1462
1561, 1503,
1468
1565, 1504,
1460
1228 1675, 1628
1222 1682, 1631
1225 1675, 1638
761
1600, 6.91 m (625) 7.68 7.50 m (5H),
1615 6.53 6.45 m (2H)
(1352) 1601 6.98 s (628) 8.52 8.11 m (5H)
8.91 8.68 d.d
(4H)
9.36 8.93 d.d
(4H)
XXII
XXIII
XXIV
XXV
(1350) 1596 7.02 s (634) 9.02 8.90 d.d (4H) 9.43 9.13 d.d
(4H)
(1352) 1602 6.99 s (629) 8.31 7.98 d.d (4H) 9.41 9.08 d.d
(4H)
1225, 1680, 1628
3562a
1254, 1678, 1630
1218
1587, 1541,
1477, 1458
(1350) 1600, 6.91 m (629) 6.77 m (2H), 7.62 s 9.39 9.06 d.d
1617
(1H), 6.15 5.94
(4H)
m
(4H)
XXVI
1545, 1501,
1452
1226 1678, 1626
1628
(1352) 1601, 6.95 m (628) 7.75 7.53 m (5H), 9.37 8.98 d.d
1617 6.64 6.54 m (2H) (4H)
XXVII 1583, 1551,
762,
1602 6.82 s (486) 8.26 8.01 d.d (8H) 8.72 8.38 d.d
(8H)
1493, 1460
(1350)
a
.
OH
The significant effects of solvent and anion X in
salts VI and VIII on the composition of the reaction
products may be due to many factors, among which
the most significant, in our opinion, are the solvation
effects and the solubilitites of the corresponding
potassium salts formed as by-products.
Mercury-containing phosphorylides X XV are
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A NEW ROUTE TO MERCURY-CONTAINING TRIPHENYLPHOSPHONIUM SALTS
533
+
O
DMF
Ph3PCC(O)Ph
C
O
H
H
R
CH3OH, 56 C
OPPh3
HgCl
Ar
X, XI +
C R
C=C
XVI
K2CO3
HgOCOCF3
IX
KBr,
CO2,
H2O
NH3, CHCl3
XVII XXVI
A = 4-BrC6H4 (XVII XXI), 4-NO2C6H4 (XXII XXVI);
R = Ph (XXVII, XXII), 4-NO2C6H4 (XVIII, XXIII);
CH3CN
XIII
colorless or pale yellow substances readily soluble in
polar organic solvents and insoluble in water. The
analytical (Table 1), H NMR, and IR data (Table 2)
4-HOC6H4 (XIX, XXIV),
CH=CH CH=CH (XX,
1
O
XXV), PhCH=CH (XXI, XXVI).
are consistent with their composition and structure.
In the IR spectra, the absorption band of the carbonyl
group in the aroyl moiety is strongly shifted toward
1
tion bands in the range 1620 1640 cm characteriz-
1
ing the stretching vibrations of the C=O bond in the
aroyl moiety conjugated with the double bond, and
also the bands of the HgOCOCF3 group. In addition,
the IR spectra contained the absorption bands of the
other functional groups present in the products (NO2,
OH, double bonds, aromatic system).
lower frequencies (1570 1560 cm ), which is typical
1
of related ylides [4, 8]. In the H NMR spectra, the
methine proton signal is absent, and the aromatic
proton signals are shifted upfield by 0.1 0.2 ppm
owing to decreased positive charge on the P atom.
Upon refluxing in 15% HCl, all the ylides X XV
eliminated mercury in the form of Hg2+, which was
quantitatively precipitated on passing H2S through the
reaction mixture.
1
The H NMR spectra (Table 2) of XVII XXVI
contain three groups of proton signals. The aryl pro-
tons are manifested in the low field as a doublet of
doublets with characteristic proton coupling constants;
the protons of radical R are manifested in the higher
field, also as a doublet of doublets for compounds
with p-substituents in the benzene ring (XVIII, XIX,
XXIII, XXIV) and as a multiplet for XVII,
XX XXII, XXV, and XXVI; olefin protons give
complex multiplets in the range 5.87 6.53 ppm. The
C H signal is observed at 6.89 7.02 ppm and is
characterized by the coupling constant JHgH as large
as 634 586 Hz. Such values of JHgH are typical
[17, 18] of the transoid arrangement of the H and Hg
atoms at the C=C bond. Hence, compounds XVII
XXVI can be identified as Z isomers.
It is known [10] that triphenylphosphonium ylides
are widely used in the Wittig reaction [15] with car-
bonyl compounds to prepare the corresponding ole-
fins. Mercury-containing symmetrical ylides XIII XV
were also used [6] in this reaction with a series of
aromatic aldehydes and trichloroacetaldehyde; the
following unsaturated mercury-containing compounds
were obtained in 43 71% yields:
3
3
R CH=C Hg C=CHR
CN
RCH=C Hg C=CHR
COOCH
CN
3 COOCH3
R = Ph, 4-MeOC6H4, 4-BrC6H4, 3-NO2C6H4, 4-NO2C6H4;
R = 4-NO2C6H4, CCl3.
An additional evidence of the Z structure of the
olefins prepared is the symmetrization reaction (see
below the example for XVIII) occurring under the
action of NH3 in CHCl3 at room temperature. The
reaction yielded a symmetrical mercury-containing
compound XXVII; in its H NMR spectrum, the ole-
fin proton signals were observed in a higher field, but
In this work, we studied new examples of the
Wittig reaction between unsymmetrical ylides X and
XI and a series of aromatic aldehydes, including those
containing double bonds. We found the best reaction
conditions: refluxing of equimolar amounts of the
reactants in a minimal volume of methanol for 1 2 h.
The resulting unsaturated organomercury compounds
precipitated on cooling, and triphenylphosphine oxide
remained in the solution. The yields of products
XVII XXVI were 30 72% (Table 1).
1
3
with approximately the same coupling constant JHgH
(Table 2) characteristic of Z isomers. We also pre-
pared XXVII by an independent synthesis: reaction of
symmetrical ylide XIV with p-nitrobenzaldehyde in
methanol. It is known [6] that such reactions yield
exclusively the Z isomers, and this was the case in our
reaction.
The compositions and structures of olefins XVII
XXVI were confirmed by elemental analysis (Ta-
Samples of compound XXVII prepared by different
1
ble 1), H NMR and IR spectra (Table 2), and chem-
routes appeared to be identical in physicochemical
1
ical transformations. The IR spectra contained absorp-
properties and in the H NMR and IR spectra.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 4 2004

534
NEVSTRUEV et al.
Br
H
H
C
NO2
O
C=C
Hg
O
NH3, CHCl3
XVIII
C=C
O2N
C
Br
XXVII
O
CH3OH, 56 C
2OPPh3
XIV + 2
NO2
C
H
EXPERIMENTAL
was stirred for 15 min at room temperature. Then
10 ml of water was added, and the mixture was
allowed to stand at 5 6 C for 15 h. The precipitate
was filtered off, washed with 5 ml of water, and dried.
Yield of ylide X 0.30 g. Ylides XI and XII were
prepared similarly.
The IR spectra were recorded on IKS-29 and
UR-20 spectrophotometers (mulls in mineral oil or
1
KBr pellets). The H NMR spectra were taken on
a Bruker WP-200SY spectrometer (200.13 MHz,
DMSO-d6, internal reference TMS).
Bis[benzoyl(triphenylphosphonio)methylido]-
mercury XIII. a. To a solution of 0.5 mmol of V in
5 ml of acetonitrile, we added 0.8 ml of a 10% aqueous
solution of potassium carbonate. The mixture was
stirred for 30 min at room temperature. Then 10 ml
of water was added, and the mixture was allowed to
stand at 5 6 C for 15 h. The precipitate was filtered
off, washed with 5 ml of water, and dried. Yield of
diylide XIII 0.16 g. Compounds XIV and XV were
prepared similarly.
[Benzoyl(trifluoroacetatomercurio)methyl]tri-
phenylphosphonium bromide V. a. A 1-mmol por-
tion of mercury(II) trifluoroacetate was added to a
solution of 1 mmol of phenacyltriphenylphosphonium
bromide I [11] in 10 ml of anhydrous ethanol. The
mixture was refluxed for 1 h. After cooling, 30 ml of
diethyl ether was added, and the mixture was allowed
to stand at 5 6 C for 15 h. The precipitate was fil-
tered off, washed with 10 ml of hexane, and dried.
Yield of salt V 0.76 g. Compounds VI VIII were
prepared similarly.
b. To 0.5 mmol of ylide X, we added 5 ml of a
saturated (at room temperature) solution of ammonia
in chloroform. The mixture was stirred for 30 min.
Then the solvent was removed in a vacuum at room
temperature, and the residue was washed with 10 ml
of water and dried. Yield of diylide XIII 0.12 g. Di-
ylides XIII XV were prepared similarly from ylides
XI, XII, and XVI.
b. To a solution of 1 mmol of benzoyltriphenyl-
phosphorylide [12] in 5 ml of ethanol, we added
1 mmol of mercury(II) trifluoroacetate and 0.2 g of
NaBr. The mixture was stirred for 30 min at room
temperature, after which 30 ml of diethyl ether was
added, and the mixture was allowed to stand at 5 6 C
for 15 h. The precipitate was filtered off, washed with
5 ml of cold water, and dried. Yield of salt V 0.75 g.
Compounds VI VIII were prepared similarly.
(Z)-1-(4-Bromophenyl)-2-trifluoroacetatomer-
curio-3-phenyl-2-propen-1-one XVII. To a solution
of 1 mmol of ylide XI in 10 ml of methanol, we added
1 mmol of benzaldehyde; the mixture was refluxed for
1 h. The precipitate that formed after cooling was
filtered off, washed with 3 ml of cold methanol, and
dried. Yield of XVII 0.44 g. Triphenylphosphine
oxide was isolated from the filtrate after methanol
evaporation; yield 82%, mp 155 156 C (from aque-
ous ethanol).
[Benzoyl(chloromercurio)methyl]triphenylphos-
phonium chloride IX. To a solution of 0.5 mmol of
salt V in 3 ml of ethanol, we added 3 ml of 20%
aqueous NaCl; the mixture was refluxed for 1 h. After
cooling, 5 ml of water was added, and the mixture
was allowed to stand at 5 6 C for 15 h. The precipi-
tate was filtered off, washed with 5 ml of cold water,
and dried. Yield of salt IX 0.32 g, mp 188 189 C [3].
Compounds XVIII XXVI were prepared similarly.
Benzoyl(trifluoroacetatomercurio)triphenyl-
phosphoniomethylide X. To a solution of 0.5 mmol
of V in 5 ml of DMF, we added 0.8 ml of a 10%
aqueous solution of potassium carbonate. The mixture
Bis[2-(4-nitrophenyl)-1-(4-bromobenzoyl)ethe-
nyl]mercury XXVII. a. To 0.5 mmol of XVIII, we
added 3 ml of a saturated (at room temperature) solu-
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A NEW ROUTE TO MERCURY-CONTAINING TRIPHENYLPHOSPHONIUM SALTS
535
tion of ammonia in chloroform. The mixture was
stirred for 30 min. The solvent was removed in a
vacuum at room temperature, and the residue was
washed with 8 ml of water and dried. Yield of XXVII
0.12 g.
8. Nesmeyanov, N.A., Novikov, V.M., and Reutov, O.A.,
Zh. Org. Khim., 1966, vol. 2, no. 6, p. 942.
9. Nevstruev, A.N., Moskalenko, A.I., and Boev, V.I.,
Zh. Obshch. Khim., 1999, vol. 69, no. 6, p. 1009.
10. Johnson, A.W., Ylide Chemistry, New York: Aca-
demic, 1966.
b. To a solution of 0.5 mmol of diylide XIV in
6 ml of methanol, we added 1 mmol of 4-nitrobenzal-
dehyde; the mixture was refluxed for 1 h. The precipi-
tate that formed after cooling was filtered off, washed
with 3 ml of cold methanol, and dried. Yield of
XXVII 0.17 g. Triphenylphosphine oxide was isolated
from the filtrate after methanol evaporation; yield
79%, mp 156 157 C (from aqueous ethanol).
11. Erastov, O.A. and Nikonov, G.A., Funktsional’noza-
meshchennye fosfiny i ikh proizvodnye (Functionally
Substituted Phosphines and Their Derivatives),
Moscow: Nauka, 1986.
12. Shevchuk, M.I. and Dombrovskii, A.V., Zh. Obshch.
Khim., 1963, vol. 33, no. 5, p. 1263.
13. Gunther, H., NMR Spectroscopy: An Introduction,
Chichester: Wiley, 1980.
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14. Makarova, L.G. and Nesmeyanov, A.N., Metody
elementoorganicheskoi khimii. Rtut’ (Methods of
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