Conversion of oximes, phenylhydrazones, 2,4-dinitrophenylhydrazones, and semicarbazones to corresponding carbonyl compounds with benzyltriphenylphosphonium peroxymonosulfate (BnPh3P+HSO5-) (BTPPMS) in the presence of bismuth chloride under non-aqueous conditions

Article abstract of DOI:10.1081/SCC-100106197

Benzyltriphenylphosphonium peroxymonosulfate (BTPPMS) (1) has been found to be an efficient and novel reagent for the conversion of oximes, phenylhydrazones, 2,4-dinitrophenylhydrazones and semicarbazones to the corresponding carbonyl compounds. The reaction has been performed in acetonitrile under reflux conditions in the presence of a catalytic amount of bismuth chloride.

Full text of DOI:10.1081/SCC-100106197

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CONVERSION OF OXIMES, PHENYLHYDRAZONES, 2,4-
DINITROPHENYLHYDRAZONES, AND SEMICARBAZONES
TO CORRESPONDING CARBONYL COMPOUNDS
WITH BENZYLTRIPHENYLPHOSPHONIUM
-
PEROXYMONOSULFATE (BnPh3P+HSO5 ) (BTPPMS) IN
THE PRESENCE OF BISMUTH CHLORIDE UNDER NON-
AQUEOUS CONDITIONS
A. R. Hajipour a , S. E. Mallakpour b , I. M. Baltork c & H. Adibi c
a Pharmaceutical Research Laboratory , College of Chemistry, Isfahan University of
Technology , Isfahan, IR, 84156, Iran
b Pharmaceutical Research Laboratory , College of Chemistry, Isfahan University of
Technology , Isfahan, IR, 84156, Iran
c Department of Chemistry , Isfahan University , Isfahan, IR, 81744, Iran
Published online: 22 Aug 2006.
To cite this article: A. R. Hajipour , S. E. Mallakpour , I. M. Baltork & H. Adibi (2001) CONVERSION OF OXIMES,
PHENYLHYDRAZONES, 2,4-DINITROPHENYLHYDRAZONES, AND SEMICARBAZONES TO CORRESPONDING CARBONYL
-
COMPOUNDS WITH BENZYLTRIPHENYLPHOSPHONIUM PEROXYMONOSULFATE (BnPh3P+HSO5 ) (BTPPMS) IN THE PRESENCE
OF BISMUTH CHLORIDE UNDER NON-AQUEOUS CONDITIONS, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 31:22, 3401-3409, DOI: 10.1081/SCC-100106197
To link to this article: http://dx.doi.org/10.1081/SCC-100106197
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SYNTHETIC COMMUNICATIONS, 31(22), 3401–3409 (2001)
CONVERSION OF OXIMES,
PHENYLHYDRAZONES, 2,4-DI-
NITROPHENYLHYDRAZONES, AND
SEMICARBAZONES TO CORRE-
SPONDING CARBONYL COMPOUNDS
WITH BENZYLTRIPHENYLPHOS-
PHONIUM PEROXYMONOSULFATE
(BnPh3PþHSOÀ5 ) (BTPPMS) IN THE
PRESENCE OF BISMUTH CHLORIDE
UNDER NON-AQUEOUS CONDITIONS
A. R. Hajipour,1, S. E. Mallakpour,1,
*
*
I. M. Baltork,2 and H. Adibi 2
1Pharmaceutical Research Laboratory,
College of Chemistry, Isfahan University of
Technology, Isfahan 84156, IR Iran
2Department of Chemistry, Isfahan University,
Isfahan 81744, IR Iran
ABSTRACT
Benzyltriphenylphosphonium peroxymonosulfate (BTPPMS)
(1) has been found to be an efficient and novel reagent for
the conversion of oximes, phenylhydrazones, 2,4-dinitrophe-
*Corresponding authors. Fax: þ98318912350; E-mail: haji@cc.iut.ac.ir
3401
Copyright & 2001 by Marcel Dekker, Inc.
www.dekker.com

ORDER
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3402
HAJIPOUR ET AL.
nylhydrazones and semicarbazones to the corresponding
carbonyl compounds. The reaction has been performed in
acetonitrile under reflux conditions in the presence of a
catalytic amount of bismuth chloride.
Oximes, phenylhydrazones, 2,4-dinitrophenylhydrazones and semicar-
bazones are highly crystalline and very useful compounds for purification
and characterization of carbonyl compounds. The above-mentioned deriva-
tives are also useful as efficient protecting groups for aldehydes and
ketones.1 Conversion of oximes into their corresponding carbonyl com-
pounds is a very important process in synthetic organic chemistry. The
classical method for the cleavage of oximes to aldehydes and ketones
includes acid hydrolysis which is not suitable for acid sensitive compounds.2
Several oxidative deoximation methods have been developed which have
found some advantages over the classical hydrolysis method.3–13 In recent
years, little attention has been paid to developing efficient and mild methods
for the oxidative cleavage of phenylhydrazones, 2,4-dinitrophenylhydra-
zones and semicarbazones and only a few reports are available on the use
of these derivatives to their corresponding carbonyl compounds.12–18
Oxoneꢀ (2KHSO5.KHSO4.K2SO4) is an inexpensive, water-soluble
and stable oxidizing reagent that is commercially available. This reagent is
insoluble in non-aqueous solvents, however, the requirement of aqueous
conditions had to be overcome. Very recently, we have introduced new
reagents for cleavage of the carbon-nitrogen double bonds under non-
aqueous and dry conditions.19,20
As part of our continued effort to develop new reagents for the
cleavage of C¼N double bond of carbonyl derivatives, we now wish to
report the synthesis of BTPPMS (1) as an efficient and novel reagent for
the oxidative cleavage of the C¼N bond of oximes, phenylhydrazones, 2,4-
dinitrophenylhydrazones and semicarbazones.21 Using BTPPMS (1) in the
presence of 0.3 molar ratio of bismuth chloride various oximes, phenylhy-
drazones, 2,4-dinitrophenylhydrazones and semicarbazones have been
successfully deprotected to afford the corresponding aldehydes and ketones
in moderate to excellent yields. The reactions are performed in acetonitrile
under reflux conditions and the results are summarized in Table 3. Notably,
aldehydes did not undergo further oxidation to their carboxylic acids under
the reaction conditions. BTPPMS (1) is a mild, efficient, stable and cheap
reagent, which has been used for our studies under non-aqueous conditions.
This reagent is a white powder, which is prepared by the dropwise addition
of an aqueous solution of Oxoneꢀ to an aqueous solution of benzyltriphe-
nylphosphonium chloride at room temperature.21 Filtration and drying of

ORDER
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CONVERSION OF OXIMES
3403
the precipitates produced a white powder, which could be stored for months
without losing its oxidation ability. The amounts of HSOÀ5 in this reagent
have been determined by an iodometric titration method.22 The measure-
ments are consistent with almost 99% (24.24 ꢀ 0.6% by weight) of active
oxidizing agent. This reagent is quite soluble in methylene chloride, chloro-
form, acetone, and acetonitrile and insoluble in non-polar solvents such as
carbontetrachloride, n-hexane, and diethyl ether.
Deoximation of acetophenone oxime to its corresponding acetophe-
none with reagent (1) in the presence of various Lewis acids such as ZnCl2,
FeCl3, BiCl3 and AlCl3 were examined in refluxing acetonitrile. Surprisingly,
only BiCl3 was shown to be effective catalyst for this purpose (Table 1). The
reaction in the presence of ZnCl2, FeCl3 and AlCl3 (0.5 mmol) proceeds with
lower efficiency even with a higher molar ratio of the oxidant (1.5 mmol) in
comparison with the amount of oxidant used in the presence of BiCl3
(0.3 mmol). This could be the effect of softness or less solubility of BiCl3
in comparison with the other Lewis acids, which have been used in these
experiments.
In order to evaluate the synergy between bismuth chloride and this
reagent, we tried several experiments. When we used acetophenone oxime
with bismuth chloride in the absence of this reagent, no deoximation was
occurred at all, but Beckman rearrangement was occurred in yield of 20%
after 60 min in refluxing acetonitrile. We also tried the reaction of acetophe-
none oxime with BTPPMS (1) in refluxing acetonitrile as well as with
Oxoneꢀ in refluxing acetonitrile and in mixture of water and acetonitrile
(50 : 50) without using any bismuth chloride. The reaction with Oxoneꢀ and
BTPPMS (1) in acetonitrile under refluxing conditions does not proceed
after 120 and 60 min respectively. When we tried the reaction of acetophe-
none oxime in a mixture of water and acetonitrile (50 : 50) with Oxoneꢀ, the
corresponding ketone obtained in 40% yield. In another reaction, we tried
the reaction of acetophenone oxime with Oxoneꢀ in the presence of a cat-
Table 1. Deoximation of Acetophenone Oxime with Reagent
(1) with Different Lewis Acids in Refluxing Acetonitrilea,b
Entry
Lewis acid
Time (hr)
Yield (%)
1
2
3
4
ZnCl2
FeCl3
AlCl3
BiCl3
0.75
0.75
0.75
0.75
30
50
60
100
b
aMonitored by TLC. Oxidant/Oxime/Lewis acid (1 : 1 : 0.3).

ORDER
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3404
HAJIPOUR ET AL.
alytic amount of BTPPMS (1) (0.2 mmol) in refluxing acetonitrile and the
reaction proceeded in 10% yield after 3 h. We also investigated the use of
Oxoneꢀ in the presence of bismuth chloride in refluxing acetonitrile and
observed that the reaction does not complete after 2 h and the corresponding
ketone was obtained in 70% yield. The results of these experiments are
summarized in Table 2.
The mildness of the reagent has been shown by the oxidative cleavage
of oximes and semicarbazones to their corresponding carbonyl compounds
in good to excellent yields (Scheme 1 and Table 3). This reagent is able to
convert phenylhydrazones derivatives to the corresponding carbonyl com-
pounds in moderate yields. When we treated a,b-unsaturated oxime or
semicarbazone, only the C¼N bond was selectively oxidized to the corre-
sponding carbonyl compound and the reagent was ineffective in oxidizing
C¼C double bond (Table 3). The mechanism of the reaction is not clear for
us at this stage.
Another noteworthy advantage of the reagent lies exclusive oxidation
of alcohols in the presence of oximes, semicarbazones or phenylhydrazones.
We have found that benzyltriphenylphosphonium peroxymonosulfate
(1) (1 mmol) and bismuth chloride (0.3 mmol) are able to oxidize alcohols
Table 2. Reaction of Acetophenone Oxime Under Refluxing Conditions
Entry
Reagent
Solvent
Lewis acid Time (min) Yielda (%)
1b
2
3
4
5c
6d
7d
–
BTPPMS
Oxoneꢀ
CH3CN
CH3CN
CH3CN
BiCl3
–
–
–
–
6
60
0
40
N.R
40
10
70
20
120
120
180
120
50
Oxoneꢀ
CH3CN-H2O
CH3CN
CH3CN
Oxoneꢀ-BTPPMS
Oxoneꢀ
BTPPMS
BiCl3
BiCl3
CH3CN
100
aMonitored by TLC. bBeckman rearrangement. cBTPPMS was used as catalytic
d
amount (0.2 mmol). Oxidant/Oxime/Lewis acid (1 : 1 : 0.3).
Scheme 1.

ORDER
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CONVERSION OF OXIMES
3405
Table 3. Conversion of Oximes, Phenylhydrazones, 2,4-Dinitrophenlhydrazones
and Semicarbazones to Carbonyl Compoundsa
Time Yield
(min) (%)b
Entry Substrate
Product
1
2
3
4
5
Benzaldoxime
3-Nitrobenzaldoxime
Acetophenone oxime
Benzophenone oxime
4-Chloroacetophenone oxime
Benzaldehyde
50
150
50
120
60
94
90
99
95
90
3-Nitrobenzaldehyde
Acetophenone
Benzophenone
4-Chloroacetophenone
64-Bromoacetophenone oxime
4-Bromoacetophenone 0
4-Phenylacetophenone
3,4-Dimethoxya-
cetophenone
6 98
7
8
4-Phenylacetophenone oxime
3,4-Dimethoxyacetophenone
oxime
75
35
92
90
9
5-Methylfurfuraldoxime
3-Methoxybenzaldoxime
Cyclohexanone oxime
9-Fluorenone oxime
a-Tetralone oxime
5-Methylfurfuraldehyde
3-Methoxybenzaldehyde
Cyclohexanone
90
40
20
45
50
60
40
88
90
85
95
93
93
85
10
11
12
13
14
15
9-Fluorenone
a-Tetralone
Cinnamaldehyde
4-Phenylcyclohexanone
Cinnamaldoxime
4-Phenylcyclohexanone oxime
16Acetophenone semicarbazone
17
Acetophenone
0
4-Bromoacetophenone
6 95
4-Bromoacetophenone
semicarbazone
120
93
18
19
Benzophenone semicarbazone
3-Methoxybenzaldehyde
semicarbazone
Benzophenone
3-Methoxybenzaldehyde
150
75
85
80
20
3-Chlorobenzaldehyde
semicarbazone
3-Chlorobenzaldehyde
100
75
21
22
23
24
4-Acetylpyridine semicarbazone 4-Acetylpyridine
a-Tetralone semicarbazone a-Tetralone
5-Methylfurfural semicarbazone 5-Methylfurfuraldehyde
150
90
120
210
70
90
80
78
3-Nitrobenzaldehyde
semicarbazone
4-Phenylacetophenone
semicarbazone
3-Nitrobenzaldehyde
4-Phenylacetophenone
Cinnamaldehyde
25
150
120
100
270
80
75
70
40
26Cinnamaldehyde
semicarbazone
27
4-Phenylcyclohexanone
semicarbazone
2-Chlorobenzaldehyde
phenylhydrazone
4-Phenylcyclohexanone
2-Chlorobenzaldehyde
28
(continued )

ORDER
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3406
HAJIPOUR ET AL.
Table 3. Continued
Time
(min)
Yield
(%)b
Entry Substrate
Product
29
30
31
32
33
3-Methoxybenzaldehyde
phenylhydrazone
3,4-Dimethoxybenzaldehyde
phenylhydrazone
Phenylacetophenone
phenylhydrazone
4-Bromoacetophenone-
2,4-DNPHc
4-Methoxyacetophenone-
2,4-DNPHc
Acetophenone-2,4-DNPHc
2-Acetylpyridine-2,4-DNPHc 2-Acetylpyridine
2-Acetylpyridine-2,4-DNPHc 3-Acetylpyridine
3-Methoxybenzaldehyde
270
210
300
300
240
35
30
20
40
20
3,4-Dimethoxy-
benzaldehyde
Phenylacetophenone
4-Bromoacetophenone
4-Methoxyacetophenone
Acetophenone
34
35
35
360
300
300
40
20
30
1
aAll products were confirmed by comparison with authentic samples (IR, H-NMR
and TLC). bYield of isolated pure carbonyl compound. c 2,4-dinitrophenyl-
hydrazone.
(1 mmol) in the presence of oximes, semicarbazones or phenylhydrazones
(1 mmol) in acetonitrile under reflux conditions and the mentioned
derivatives remain unchanged (Eqs. 1–3). We also observed that in the
presence of an equimolar amount of oxime and semicarbazone by using
benzyltriphenylphosphonium peroxymonosulfate (1) (1 mmol) and bismuth
chloride (0.3 mmol) only oxime was selectively oxidized in refluxing
acetonitrile (Eq. 4).
In conclusion, we have reported a new and efficient reagent for the
regeneration of aldehydes and ketones from their derivatives under non-
aqueous and aprotic conditions. The stability, easy preparation of the
reagent, easy work-up and high yields of the products make this reagent a
novel and useful oxidizing one relative to the reported reagents for regen-
eration of carbonyl compounds from their derivatives and makes this
compound a bench-top oxidizing agent.
EXPERIMENTAL
All yields refer to isolated products. Products were characterized by
1
comparison with authentic samples (IR and H-NMR spectrum, melting

ORDER
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CONVERSION OF OXIMES
3407
1
and boiling point and TLC analysis).19–21,23,24 All H-NMR spectra were
recorded at 90 MHz in CDCl3 and CCl4 relative to TMS (0.00 ppm). The
Research Institute of Petroleum Industry, Tehran, I.R. Iran performed
elemental analysis.
Preparation of Benzyltriphenylphosphonium
Peroxymonosulfate (1)
A solution of benzyltriphenylphosphonium chloride (7.76g, 20 mmol)
in 100 ml of water was prepared, then oxoneꢀ (2KHSO4.KHSO4.K2SO4,
12.28 g, 20 mmol) in water (100 ml) was added dropwise to the above
solution and stirred for 1 h at room temperature. The resulting precipitate
was filtered and washed with cooled distilled water (50 ml), and dried in a
desiccator under a vacuum over calcium chloride to afford a white powder
(21.7 g, 95% yield), which decomposed at 144–146ꢁC to a dark-brown
material. 1H-NMR: d 7.93–6.87 (m, 20H), 4.7 (d, J ¼ 25.6Hz, CH2-P).
IR (KBr): 1298, 1269, 1098, 1060, 700, 658, 590 cmÀ1. The white solid
was then titrated three times as following procedure:22 To a 0.244 g
sample was added 0.5 ml of glacial acetic acid and 1 ml of 10% aqueous
NaI. After dilution of 5 ml with THF, it was titrated with 5.20 ml of
0.1012 M solution of sodium sulfite to the yellow endpoint. The average
of the three trials gave 99% (24.24 ꢀ 0.6% by weight) of active oxidizing

ORDER
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3408
HAJIPOUR ET AL.
agent (HSOÀ5 ). Found: C, 64.20; H, 5.20; S 6.60%. Calcd for C25H23O5PS:
C, 64.37; H, 4.97; S 6.87%.
Conversion of Oximes, Phenylhydrazones,
2,4-Dinitrophenylhydrazones and Semicarbazones
to the Corresponding Carbonyl Compounds with
Reagent (1)
Typical Procedure
A solution of acetophenone oxime (0.135 g, 1 mmol) and BiCl3
(0.094 g, 0.3 mmol) in acetonitrile (5 ml) was prepared. Benzyltriphenylphos-
phonium peroxymonosulfate (0.466 g, 1 mmol) was added to this solution
and refluxed for 50 min. TLC followed the reaction progress. The mixture
was allowed to reach to room temperature and then was filtered. The solid
material was washed with acetonitrile (15 ml). Removal of solvent and the
resulting crude material on purification by column chromatography on silica
gel with appropriate eluent gave the corresponding acetophenone in 99%
yield (Table 3).
Competitive Reactions
Typical Procedure
A mixture of acetophenone oxime (0.14 g, 1 mmol), 3-methoxybenzal-
dehyde semicarbazone (0.19 g, 1 mmol) and BiCl3 (0.094 g, 0.3 mmol) were
added to a stirred solution of the oxidant (1) (0.47 g, 1 mmol) in acetonitrile
(5 ml). The reaction mixture was heated at reflux until TLC showed com-
plete disappearance of acetophenone oxime (75 min). The other competitive
reactions for Eqs. 1–3 were carried out under similar conditions.
ACKNOWLEDGMENT
We are thankful to the Isfahan University of Technology Research
Council for the partial support of this work.
REFERENCES
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Wiley, New York, 1991.

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CONVERSION OF OXIMES
3409
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Received in Japan August 30, 2000

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