The first example of ligand-mediated dehydration of aldoximes

Article abstract of DOI:10.1016/S0020-1693(03)00275-5

The nitrile complex trans-[PtCl₄(EtCN)₂] reacts with the aldoximes HON=C(H)R [R=C(Ph)(=O), Me, Ph] in CH₂Cl₂ to afford products of the addition of the aldoxime HON group across the nitrile CN triple bond, i.e. trans-[PtCl₄{NH=C(Et)ON=C(H)R}₂] (1-3). These compounds were characterized by elemental analyses, FAB MS, IR and ¹H and ¹³C{¹H} spectroscopies and X-ray structure determination has been performed for 1. In CHCl₃ solution, 1-3 undergo the spontaneous imine ligand splitting to achieve the carboxamide complex trans-[PtCl₄{NH=C(Et)OH}₂] and RCN thus giving the first example of a ligand-mediated dehydration of aldoximes. The carboxamide and RCN products are also formed upon treatment of trans-[PtCl ₄(EtCN)₂] with 2 equiv. of HON=C(H)R in CH ₂Cl₂.

Full text of DOI:10.1016/S0020-1693(03)00275-5

Inorganica Chimica Acta 356 (2003) 382Á386
/
www.elsevier.com/locate/ica
Note
The first example of ligand-mediated dehydration of aldoximes
Anastassiya V. Makarycheva-Mikhailova a, Nadezhda A. Bokach a, Matti Haukka b,
Vadim Yu. Kukushkin a,*
a Department of Chemistry, St. Petersburg State University, 198504 Stary Petergof, Russia
b Department of Chemistry, University of Joensuu, P.O. Box 111, FIN-80101 Joensuu, Finland
Received 28 February 2003; accepted 25 April 2003
Dedicated to Prof. Dr. J.J.R. Frau´sto da Silva on the occasion of his retirement
Abstract
The nitrile complex trans-[PtCl4(EtCN)2] reacts with the aldoximes HONÄ
/
C(H)R [Rꢀ
/
C(Ph)(Ä
/
O), Me, Ph] in CH2Cl2 to afford
C(Et)ONÄC(H)R}2]
3). These compounds were characterized by elemental analyses, FAB MS, IR and H and 13C{1H} spectroscopies and X-ray
structure determination has been performed for 1. In CHCl3 solution, 1Á3 undergo the spontaneous imine ligand splitting to achieve
the carboxamide complex trans-[PtCl4{NHÄC(Et)OH}2] and RCN thus giving the first example of a ligand-mediated dehydration
products of the addition of the aldoxime HON group across the nitrile CN triple bond, i.e. trans-[PtCl4{NHÄ
/
/
1
(1Á
/
/
/
of aldoximes. The carboxamide and RCN products are also formed upon treatment of trans-[PtCl4(EtCN)2] with 2 equiv. of HONÄ
/
C(H)R in CH2Cl2.
# 2003 Elsevier B.V. All rights reserved.
Keywords: Aldoximes; Dehydration; Nitrile complexes; Platinum(IV) complexes; Hydrolysis; Ligand-mediated reaction
1. Introduction
imes by the strong nonionic base P[NR(CH2)2]3N [15] or
on heterogeneous ruthenium catalyst prepared by ad-
sorption of [RuCl2(p-cymene)]2 on activated carbon [16]
or on molecular sieves [17]. In addition, studies on
enzymatic systems, i.e. aldoxime dehydratases [18,19]
and cytochrome P 450 [20], and their application to
nitrile synthesis have been reported.
Being interested in the chemistry of both oximes and
nitriles (for reviews see [21,22]), we studied the reaction
between the platinum(IV) complex trans-[PtCl4(EtCN)2]
and aldoximes and found the first example of ligand-
Aldoximes are used as convenient precursors for the
synthesis of the corresponding nitriles by the dehydra-
tion and this gives strong motivation for an active search
of systems to achieve this useful transformation [1].
Recent activities in this area include application of some
organic reagents (e.g. sulfonyl chlorides RSO2Cl [2],
SOCl2 in combination with polyvinylpyrrolidone [3] or
benzotriazole [4], trifluoromethanesulfonic anhydride/
triethylamine [5] and PPh3/N-chlorosuccinimide [6]
systems, the Burgess reagent [7], phthalic anhydride
under microwave irradiation [8]) and inorganic materials
(e.g. solid metaboric acid [9], NaHSO4 in xylenes [10],
Na2O, K2O, or BaO on alumina, titania, silica, or
zirconia [11], In(III) [12], Ti(IV) [13], Fe(II) [14] salts).
There are also examples, albeit rather rare, of catalytic
dehydration of aldoximes, e.g. the conversion of aldox-
mediated dehydration of HONÄ
/
CHR species, particu-
larly by the coordinated nitriles, and these results are
reported herein.
2. Results and discussion
As a continuation of our studies on nitrileÁ
coupling involving metal centers [23Á26], we have
recently observed that the reaction between dione
monoximes HONÄ alkyl,
C(R1)C(R2)(ÄO) (R1, R2ꢀ
aryl) and platinum(IV) nitrile complexes [PtCl4(RCN)2]
/oxime
/
* Corresponding author. Tel.: ꢁ
/
7-812-428-4582; fax: ꢁ7-812-428-
/
/
/
/
6939.
E-mail address: kukushkin@VK2100.spb.edu (V.Yu. Kukushkin).
0020-1693/03/$ - see front matter # 2003 Elsevier B.V. All rights reserved.
doi:10.1016/S0020-1693(03)00275-5

A.V. Makarycheva-Mikhailova et al. / Inorganica Chimica Acta 356 (2003) 382Á
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386
383
(Rꢀ
/
Me, Et) leads, instead of the conventional sub-
stitution characteristic for these classic chelating ligands,
approximately 2 h at 35 8C) and allowed the identifica-
tion of the reaction products, i.e. the carboxamide
to the metal-mediated coupling giving iminoacylated
complex trans-[PtCl4{NHÄ
scribed by us [28]) and PhC(Ä
B). These products were also identified by comparison
O)CN
/
C(Et)OH}2] (previously de-
species
C(R1)C(R2)(Ä
the coupling reaction to another dione monoxime, i.e.
HONÄC(H)C(Ph)(ÄO), having the aldoxime moiety
containing
the
[PtIV]Á
/
N(H)Ä
/
C(R)ONÄ
/
/O)CN (Scheme 1, route
/
O) linkage [27]. We have now extended
with trans-[PtCl4{NHÄ
/
C(Et)OH}2] and PhC(Ä
/
/
/
prepared by the independent routes [28,29]. Further-
and, with the nitrile complex trans-[PtCl4(EtCN)2],
more, the treatment of trans-[PtCl4(EtCN)2] with 2
observed the same type of the addition (Scheme 1, route
equiv. of HONÄ
for approximately 3 h also gives trans-[PtCl4{NHÄ
C(Et)OH}2] and PhC(ÄO)CN.
The nitrileÁaldoxime coupling was also performed
using the aldoximes HONÄC(H)R (RꢀMe, Ph) and
/
C(H)C(Ph)(Ä
/
O) in CHCl3 at 35 8C
A) which yields the compound trans-[PtCl4{NHÄ
/
/
C(Et)ONÄC(H)C(Ph)(ÄO)}2] (1). The latter was struc-
/
/
/
/
turally characterized and the X-ray structure determina-
tion verified its trans-configuration with the newly
formed ligands in the E-configuration and H-bonding
between the imino H atom and the oxime N atom
(Figure in Scheme 1). Inspection of the bond lengths and
angles indicates a good agreement with those of the
corresponding platinum(IV) complexes [27].
/
/
the imino complexes 2 and 3 (Scheme 1) were formed
similarly to 1. However, the ligand splitting occurred
slower and the complete conversion of 2 and 3 to the
carboxamide complex and RCN takes approximately 1
week at 35 8C. All these observations together give the
first example of ligand-mediated dehydration of aldox-
imes. Taking into account, on one hand, significant
similarities in reactivity between Pt(IV)-bound nitriles
and nitrilium salts and, on the other hand, the enormous
stability of imines ligated to Pt(IV) centers [23], it is
anticipated that the nitrile ligand-mediated dehydration
can be used for modeling of highly unstable intermedi-
ates in a nitrilium ion catalyzed Beckmann rearrange-
ment [30].
In contrast to the previously described trans-
[PtCl4{N(H)Ä
/
C(R)ONÄ
/
C(R1)C(R2)(Ä
/
O)}2] (R1, R2ꢀ
alkyl, aryl) complexes [27], which exhibit substantial
/
inertness towards both hydrolysis and overall degrada-
tion, the complex 1 (R1ꢀ
H), being dissolved in chloro-
form, is involved in a further reaction. Monitoring of
/
1
the reaction by H and 13C{1H} NMR, TLC and ESI
MS showed the complete disappearance of the starting
complex 1 (approximately 1 day at 20Á25 8C or
/
˚
Scheme 1. Nitrile ligand-mediated dehydration of aldoximes. Selected bond lengths (A) and angles (8) for 1 are: Pt(1)Ã
/
N(1) 2.021(5), Pt(1)Ã
N(2) 1.443(6), N(2)ÃC(4) 1.256(8), C(4)Ã
Cl(1) 93.99(14), N(1)ÃPt(1)ÃCl(2) 85.15(15), C(1)Ã
C(3) 127.8(6), C(4)ÃN(2)ÃO(1) 111.1(5), N(2)ÃC(4)ÃC(5)
H(1) 1.03(7), H(1) N(2) 1.96(7), N(1)ꢀ ꢀ ꢀN(2) 2.533(7), N(1)Ã
ꢀ ꢀ ꢀ
/
Cl(1)
2.3113(16), Pt(1)Ã
1.516(9), C(5)ÃO(2) 1.222(8), C(5)Ã
N(1)ÃPt(1) 135.7(4), N(1)ÃC(1)ÃO(1) 120.9(5), C(1)Ã
116.7(6), O(2)ÃC(5)ÃC(4) 115.2(6), C(6)ÃC(5)ÃC(4) 122.1(5); hydrogen bond: N(1)Ã
H(1) N(2) 112(5).
ꢀ ꢀ ꢀ
/
Cl(2) 2.3204(16), N(1)Ã
C(6) 1.458(10), Cl(1)Ã
O(1)Ã
/
C(1) 1.268(8), C(1)Ã
Pt(1)Ã
N(2) 110.9(4), N(1)Ã
/
C(3) 1.499(9), C(1)Ã
Cl(2) 89.93(7), N(1)Ã
C(1)Ã
/
O(1) 1.354(7), O(1)Ã
/
/
/
C(5)
/
/
/
/
/
Pt(1)Ã
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/

384
A.V. Makarycheva-Mikhailova et al. / Inorganica Chimica Acta 356 (2003) 382Á386
/
3. Experimental section
3.1. Materials and instrumentation
Table 1
Crystal data for trans-[PtCl4{NHÄ
/
C(Et)ONÄ
/
C(H)C(Ph)(ÄO)}2] (1)
/
Empirical formula
Formula weight
Temperature (K)
C22H24Cl4N4O4Pt
745.34
150(2)
Solvents were obtained from commercial sources and
used as received. trans-[PtCl4(EtCN)2] and phenylglyox-
ynitrile were prepared accordingly to the published
methods [28,29]. The aldoximes were purchased from
Aldrich, while acetonitrile and benzonitrile were ob-
tained from Fluka. Melting points were determined on a
˚
l (A)
0.71073
monoclinic
P21/n
Crystal system
Space group
˚
a (A)
13.2151(4)
7.6789(4)
14.1884(5)
110.525(2)
1348.40(9)
2
˚
b (A)
˚
c (A)
b (8)
Buchi B-540 melting point apparatus and are uncor-
¨
3
V (A )
˚
rected. For TLC, Merck 60 F254 SiO2-plates have been
used. Positive-ion FAB mass spectra were obtained on a
Trio 2000 instrument by bombarding 3-nitrobenzyl
alcohol matrices of the samples with 8 keV (approxi-
Z
rcalc (Mg m3)
1.836
5.635
m(Mo Ka) (mmꢃ1
)
a
R1 (I ]
/
2s)
0.0320
0.0767
b
wR2 (I ]
/2s)
mately 1.28ꢂ
1015 J) Xe atoms. Mass calibration for
data system acquisition was achieved using CsI. ES mass
/
a
R1ꢀ
wR2ꢀ
/
ajjFojꢃ
/
jFcjj/ajFoj.
TM
spectra were obtained on a Bruker esquire3000 (ESI)
b
/
[a[w(Fo2ꢃ
/
Fc2)2]/a[w(Fo2)2]]1/2
.
instrument. Infrared spectra (4000Á
400 cmꢃ1) were
/
recorded on a PerkinÁElmer FTIR instrument in KBr
/
pellets. H and 13C{1H} NMR spectra were measured
on Bruker AMX 300 spectrometers at ambient tempera-
ture in CDCl3.
1
3.2.2. trans-[PtCl4{NHÄ
/
C(Et)ONÄ
/
C(H)C(Ph)(Ä
/
O)}2] (1)
Anal. Calc. for C22H24N4Cl4O4Pt: C, 35.45; H, 3.25;
N, 7.52. Found: C, 35.25; H, 3.34; N, 7.24%. FABꢁ-
3.1.1. X-ray structure determination of 1
The X-ray diffraction data was collected on a Nonius
MS, m/z: 708 [Mꢃ
on Merck 60 F254: Rfꢀ
3278 m-w n(NÃH), 1673 s and 1647 s n(CÄ
N), 1174 m n(CÃ
/
HCl]ꢁ. M.p.ꢀ
/
134 8C (dec.). TLC
0.32 (eluent CH2Cl2). IR, cmꢃ1
O) and n(CÄ
O). H: 1.41 (t, JHH 7.4 Hz, 3H, Ã
/
:
KappaCCD diffractometer using Mo Ka radiation (lꢀ
/
/
/
/
˚
0.71073 A). The Denzo-Scalepack [31] program package
1
3
/
/
was used for cell refinements and data reduction. The
structure was solved by direct methods using the SIR-97
program [32]. An empirical absorption correction based
on equivalent reflections [33] was applied to the data
(Tmax/Tmin was 0.37954/0.20739). The structure refine-
ment was carried out with the SHELXL-97 [34] program
and the WinGX graphical user interface [35]. NH
hydrogen was located from the difference Fourier map
and refined isotropically. Other hydrogens were placed
in idealized position and constrained to ride on their
parent atom. Crystallographic data is summarized in
Table 1.
3
CH2CH3), 3.35 (q, JHH 7.4 Hz, 2H, Ã
(m, 2H, PhÃHmeta), 7.63 (m, 1H, PhÃHpara), 8.08 (m,
2H, PhÃHortho), 8.31 (s, 1H, CH), 8.67 (s, br, 1H, Ã
NH Ã CH3), 25.61 (ÃCH2CH3),
). 13C{1H}: 10.07 (Ã
129.73 and 130.40 (PhÃCmeta and PhÃCortho), 132.07
(PhÃCipso), 135.83 (PhÃCpara), 153.79 (CH), 179.14 (PtÃ
NÄC Ã), 188.96 (CÄO). Crystals of 1 for the X-ray study
were obtained by evaporation of its CDCl3 solution in
open air at 20Á25 8C.
/CH2CH3), 7.49
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
/
3.2.3. trans-[PtCl4{NHÄ
/
C(Et)ONÄ
/
C(H)Me}2](2)
Anal. Calc. for C10H20N4Cl4O2Pt: C, 21.24; H, 3.54;
N, 9.91. Found: C, 21.06; H, 3.52; N, 9.67%. FABꢁ-
3.2. Synthetic work and characterization
MS, m/z: 529 [Mꢃ
Merck 60 F254: Rfꢀ
3270 m-w n(NÃH), 1642 s n(CÄ
1.34 (t, JHH 7.4 Hz, 3H, Ã
/
Cl]ꢁ. M.p.ꢀ
164 8C (dec.). TLC on
/
/
0.61 (eluent CHCl3). IR, cmꢃ1
:
3.2.1. Reaction of trans-[PtCl4(EtCN)2] with RCHÄ
/
/
/
N), 1196 m n(CÃ
/
O). 1H:
NOH (RꢀPhC(ÄO), Me, Ph)
/
/
3
/
CH2CH3), 2.13 (d, 3H, Ã
CH3), 3.29 (q, JHH 7.4 Hz, 2H, ÃCH2CH3), 7.42 (q,
1H, ÄCH), 8.68 (s, br, 1H, ÃNH Ã
). 13C{1H}: 10.03 (Ã
CH2CH3), 13.82 (ÃCH3), 25.69 (ÃCH2CH3), 156.88
(CH), 177.58 (PtÃNÄC Ã).
/
The aldoxime (0.11 mmol) was added to a solution of
trans-[PtCl4(EtCN)2] (25 mg, 0.055 mmol) in CH2Cl2 (2
ml) and the mixture was kept for 2 h at room
temperature, whereupon the solvent was removed in
vacuo at room temperature to give an oily residue which
was crystallized under diethyl ether (5 ml). The yellow
crystalline product thus formed was isolated by filtra-
tion, washed twice with 3-ml portions of diethyl ether
and dried in vacuo at room temperature. Yields are 46,
78 and 70%, respectively.
3
/
/
/
/
/
/
/
/
/
/
3.2.4. trans-[PtCl4{NHÄ
/
C(Et)ONÄ
/
C(H)Ph}2] (3)
Anal. Calc. for C20H24N4Cl4O2Pt: C, 34.85; H, 3.51;
N, 8.13. Found: C, 34.57; H, 3.67; N, 7.95%. FABꢁ-
MS, m/z: 651 [Mꢃ
/
HCl]ꢁ. M.p.ꢀ
156 8C (dec.). TLC
/

A.V. Makarycheva-Mikhailova et al. / Inorganica Chimica Acta 356 (2003) 382Á
/
386
385
on Merck 60 F254: Rfꢀ
/
0.38 (eluent: Me2CO:n-C6H12ꢀ
H), 1651 and 1619 s
O). H: 1.40 (t, 3JHH 7.4 Hz, 3H,
/
4. Supplementary material
1:4, v/v). IR, cmꢃ1: 3282 m-w n(NÃ
/
1
Crystal data have been deposited at the Cambridge
Crystallographic Data Centre (CCDC) with deposition
number CCDC 205089. Copies of this information may
be obtained free of charge from The Director, CCDC,
12 Union Road, Cambridge, CB2 1EZ, UK (fax: ꢁ44-
1223-336-033; e-mail: deposit@ccdc.cam.ac.uk or www:
http://www.ccdc.cam.ac.uk).
n(CÄ
CH2CH3), 3.32 (q, JHH 7.4 Hz, 2H, Ã
(t, 2H, PhÃHmeta), 7.57 (m, 1H, PhÃHpara), 7,76 (d, 2H,
PhÃHortho), 8.57 (s, 1H, CH), 8.82 (s, br, 1H, ÃNH Ã).
13C{1H}: 11.08 (Ã
CH2CH3), 25.84 (ÃCH2CH3), 128.73
(PhÃCipso), 129.40 and 129.72 (PhÃ
Cortho), 133.51 (PhÃ
NÄC Ã).
/
N), 1187 m n(CÃ
/
3
Ã
/
/
CH2CH3), 7.50
/
/
/
/
/
/
/
/
/
/
Cmeta and PhÃ
/
/
Cpara), 157.49 (CH), 173.78 (PtÃ
/
/
/
Acknowledgements
3.3. Dehydration of aldoximes and ligand splitting in
trans-[PtCl4{NHÄC(Et)ONÄC(H)R}2]
We thank the Russian Fund for Basic Research for
the grant 03-03-32363. A.V.M.-M. is indebted to the
Governor of St. Petersburg for a fellowship (grant M01-
2.5D-446). A.V.M.-M. and V.Yu.K. express gratitude to
the International Science Foundation (Soros Founda-
tion) for the Soros Fellowship and Soros Professorship,
correspondingly. We thank Dr. A.A. Nazarov for
measuring ESI mass spectra and Prof. B.K. Keppler
for putting some facilities at authors disposal.
/
/
The complex trans-[PtCl4{NHÄ
/
C(Et)ONÄ
/
C(H)R}2]
(1Á
/
3) (20 mg) was dissolved in CDCl3 (1 ml) and heated
at 35 8C and the progress of the reaction was monitored
by NMR, TLC and ESI-MS; the reaction is complete
after approximately 2 h (1) or 1 week (2 and 3). In all
three cases, the previously described complex trans-
[PtCl4{NHÄ
410 [MꢃLꢁ
(eluent Me2CO:CH2Cl2ꢀ
Hz, 3H, Ã
CH2CH3), 6.91 (s, br, 1H, Ä
OH); 13C{1H}: 11.04 (Ã
CH2CH3), 30.09 (Ã
181.63 (PtÃNÄC Ã)) was detected in the reaction mix-
ture. In addition, the corresponding nitriles, i.e. PhC(Ä
O)CÅ Hꢁ
(ESI-MSꢁ (CH2Cl2), m/z: 150 [Mꢁ
H2O]ꢁ; ESI-MSꢃ (CH2Cl2), m/z: 131 [M]ꢃ; TLC on
Merck 60 F254: Rfꢀ0.53 (eluent: Me2CO:n-C6H12ꢀ
1:4, v/v); H: 7.58 (t, 2H, PhÃHmeta), 7.81 (t, 1H, PhÃ
Hpara), 8.17 (d, 2H, PhÃ
Hortho); 13C{1H}: 113.15 (C Ä
N), 129.95 and 130.92 (PhÃCmeta and PhÃCortho), 133.11
(PhÃCipso), 137.29 (PhÃCpara), 168.32 (C ÄO)); MeCÅ
(1H: 2.03 (CH3); 13C{1H}: 2.36 (CH3) and 117.53 (CN));
PhCÅN (ESI-MS (CH2Cl2), m/z: 104 [Mꢁ
H]ꢁ, 122
[MꢁHꢁ 0.50
H2O]ꢁ; TLC on Merck 60 F254: Rfꢀ
(eluent: Me2CO:n-C6H12ꢀ
1:4, v/v); 1H: 7.47 (t, 2H,
PhÃHmeta), 7.61 (m, 1H, PhÃHpara), 7.90 (d, 2H, PhÃ
Hortho); 13C{1H}: 114.33 (CÅ
N), 128.08 (PhÃCipso),
129.52 and 129.81 (PhÃCmeta and PhÃCortho), 133.78
(PhÃCpara)), were detected by the corresponding meth-
ods. All these products were additionally identified by
comparison with (i) trans-[PtCl4{NHÄC(Et)OH}2], pre-
pared by an independent route [28], and (ii) commer-
cially available nitriles (MeCN, PhCN) and PhC(Ä
/
C(Et)OH}2] [28] (ESI-MS (CH2Cl2), m/z:
/
/
H]ꢁ, 373 [Mꢃ
/
LÃ
/
Cl]ꢁ; TLC Rfꢀ
0.47
/
3:1, v/v); 1H: 1.32 (t, 3JHH 7.4
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/
3
/
CH2CH3), 2.73 (q, JHH 7.4 Hz, 2H, Ã
/
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