Facile AlCl3-promoted catalytic beckmann rearrangement of ketoximes

Article abstract of DOI:10.1080/00397911003629416

Aluminum chloride, an inexpensive and commercially available Lewis acid traditionally employed for Beckmann rearrangement with stoichiometric amounts, has been now found to smoothly promote the Beckmann rearrangement of various ketoximes to the corresponding amides (up to 99% of yield) with 10mol% catalyst loading in anhydrous acetonitrile under reflux temperature.

Full text of DOI:10.1080/00397911003629416

This article was downloaded by: [Central Michigan University]
On: 13 October 2014, At: 09:52
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered
office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic Organic
Chemistry
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/lsyc20
Facile AlCl -Promoted Catalytic
3
Beckmann Rearrangement of Ketoximes
a
a
a
a
a
Li-Feng Liu , Hua Liu , Hong-Jun Pi , Shuo Yang , Min Yao
,
a
a
Wenting Du & Wei-Ping Deng
a
School of Pharmacy, East China University of Science and
Technology , Shanghai, China
Published online: 02 Feb 2011.
To cite this article: Li-Feng Liu , Hua Liu , Hong-Jun Pi , Shuo Yang , Min Yao , Wenting Du & Wei-
Ping Deng (2011) Facile AlCl -Promoted Catalytic Beckmann Rearrangement of Ketoximes, Synthetic
3
Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry,
41:4, 553-560, DOI: 10.1080/00397911003629416
To link to this article: http://dx.doi.org/10.1080/00397911003629416
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the
“
Content”) contained in the publications on our platform. However, Taylor & Francis,
our agents, and our licensors make no representations or warranties whatsoever as to
the accuracy, completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content
should not be relied upon and should be independently verified with primary sources
of information. Taylor and Francis shall not be liable for any losses, actions, claims,
proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or
howsoever caused arising directly or indirectly in connection with, in relation to or arising
out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,
systematic supply, or distribution in any form to anyone is expressly forbidden. Terms &

Conditions of access and use can be found at http://www.tandfonline.com/page/terms-
and-conditions

1
Synthetic Communications , 41: 553–560, 2011
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397911003629416
FACILE AlCl -PROMOTED CATALYTIC BECKMANN
3
REARRANGEMENT OF KETOXIMES
Li-Feng Liu, Hua Liu, Hong-Jun Pi, Shuo Yang, Min Yao,
Wenting Du, and Wei-Ping Deng
School of Pharmacy, East China University of Science and Technology,
Shanghai, China
Abstract Aluminum chloride, an inexpensive and commercially available Lewis acid tra-
ditionally employed for Beckmann rearrangement with stoichiometric amounts, has been
now found to smoothly promote the Beckmann rearrangement of various ketoximes to
the corresponding amides (up to 99% of yield) with 10 mol% catalyst loading in anhydrous
acetonitrile under reflux temperature.
Keywords Aluminum chloride; Beckmann rearrangement; ketoxime
INTRODUCTION
The Beckmann rearrangement of ketoximes is a fundamental and commonly
used organic synthesis tool for the formation of corresponding amides through a
[1]
Brønsted acid–mediated catalytic cycle. One of the most important industrial
applications of this rearrangement reaction is the transformation of cyclohexanone
oxime into caprolactam, which is the raw material (monomer) in the production of
polymer nylon. The rearrangement, however, requires harsh conditions such as the
use of corrosive Brønsted acid, high temperature, and generation of a considerable
[
2]
amount of ammonium sulfate by-product. Hence, over the past half century,
extensive efforts have been devoted to the optimization of the catalytic reaction sys-
[
tem. Many catalytic systems such as liquid-phase system, vapor-phase system,
supercritical water system, and ionic liquid system have been developed so far.
Liquid-phase catalytic Beckmann rearrangement under mild conditions has become
a topic of current interest because of its advantages such as easy workup and
3]
[4]
[5]
[6]
Received September 29, 2009.
Address correspondence to Wei-Ping Deng and Wenting Du, School of Pharmacy, East China
University of Science and Technology, 130 Meilong Road, Shanghai 200237, China. E-mail:
weiping_deng@ecust.edu.cn; duwt@ecust.edu.cn
5
53

554
L.-F. LIU ET AL.
industrial practicability. As a consequence, various catalysts such as inorganic
catalysts, organocatalysts, and metallic Lewis acid systems were developed.
Especially for the metallic Lewis acid, a number of catalytic systems have been
[
7]
[8]
[9]
[10]
reported recently, such as [RhCl(cod)] , Yb(OTf)3, Y(OTf)3, Ga(OTf)3,
2
[
11]
[12]
[13]
Nd(OTf)3, RuCl3, and HgCl2. However, because of drawbacks such as tox-
icity, high cost, and relatively low catalytic activities (10–50 mol% catalyst loading),
these catalysts have not yet been industrially utilized.
[14]
Aluminum chloride (AlCl3)
has been widely employed for the Beckmann
rearrangement over the past half century; however, stoichiometric amounts or
even an excess amount of reagent was needed. In the course of developing a new,
[
15]
practically catalytic Beckmann rearrangement protocol, we found that TsCl,
[
16]
BOPCl, and triphosphazene, 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-chloride
[
17]
(TAPC)
can efficiently promote the Beckmann rearrangement with catalytic
amounts via a new proposed mechanism. Consequently, we further reasoned that
aluminum chloride as partially covalent metal chloride might promote the Beckmann
rearrangement as well with catalytic amount via a mechanism similar to that of
TsCl or BOPCl. In this communication, we described our preliminary results of the
AlCl -catalyzed Beckmann rearrangement of ketoximes to corresponding amides.
3
RESULTS AND DISCUSSION
Initially, acetophenone oxime was chosen as the model molecule for the
Beckmann rearrangement using 10 mol% of AlCl in anhydrous CH CN at refluxing
3
3
temperature. To our amazement, the rearrangement proceeded very smooth, afford-
ing acetanilide in 96% yield. Next, a further solvent screening showed that anhydrous
acetonitrile gave the optimal result (entries 1–4, Table 1).
With this encouraging result, we next turned to explore the generality and scope
of the AlCl -promoted Beckmann rearrangement catalytic system. A series of
3
representative ketoximes as substrates were examined under the same conditions,
and the results are summarized in Table 2. It is clear that excellent yields were obtained
for the rearrangement of all diarylketoneoximes into corresponding amides. For the
substituted acetophenone oximes, the rearrangements were generally effective;
Table 1. Aluminum trichloride (10 mol%)–catalyzed Beckmann
rearrangement of acetophenone oxime
Entry
Solvent
Yield (%)
1
2
3
4
5
THF
Toluene
Dioxane
Trace
Trace
Trace
Trace
96
CH
CH
2
Cl
CN
2
3

BECKMANN REARRANGEMENT OF KETOXIMES
555
Table 2. Scope of AlCl
3
-catalyzed Beckmann rearrangement
1
R
2
Entry
R
Yield (%)
96
1(2a)
2(2b)
3(2c)
4(2d)
Me
99
a
99
b
88
c
93
5(2e)
d
6(2f)
7(2g)
8(2h)
99
Me
Me
90
93
9
1
(2i)
Me
Me
20
78
0(2j)
1
1(2k)
2(2l)
Et
91
60
1
Me
(
Continued )

556
L.-F. LIU ET AL.
Table 2. Continued
1
2
2
R
Entry
R
Yield (%)
1
3(2m)
4(2n)
(CH
)
11
76
1
(CH
2
)
5
Trace
a
Overall yield of isomeric mixtures
Overall yield of isomeric mixtures
.
b
c
.
Overall yield of isomeric mixtures
.
.
d
Overall yield of isomeric mixtures
however, the oxime with ortho-methoxy dramatically lowered the yield to 20%, and the
electron-withdrawing para-chloro group decreases the reaction activity (60% yield,
entry 12). The Beckmann rearrangement of cyclododecanone oxime using the same
condition gave the laurolactam in good yield (76% yield, entry 13). Unfortunately,
the rearrangement of cyclohexanone oxime gave only a trace amount of e-caprolactam.
CONCLUSIONS
In conclusion, we have developed a highly efficient aluminum chloride (AlCl )–
3
promoted Beckmann rearrangement system in anhydrous acetonitrile under reflux
conditions. The procedure offers several advantages including good yields, short
reaction times, easily and cheaply obtained catalyst, and simple experimental
isolation procedures, which make the new catalytic system a potentially practical
procedure for the Beckmann rearrangement.
EXPERIMENTAL
All solvents were distilled under standard procedures prior to use under a nitro-
gen atmosphere. (For example, CH CN was distilled from CaH ; tetrahydrofuran
3
2
1
THF), dioxane, and toluene were distilled from sodium.) H (400-MHz) chemical
(
shifts are reported in CDCl , 7.27 ppm, and standards and coupling constants (J)
3
are reported in hertz (Hz). The following abbreviations are used to designate signal
multiplicity: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; and br, broad.
General Procedure for AlCl -Promoted Catalytic Beckmann
3
Rearrangement of Ketoximes
To a solution of ketoxime (2 mmol) in dry CH CN (2 mL) under N , 2 mL
3
2
CH CN (aluminum trichloride in CH CN solvent, 0.1 M=L) were added. The solvent
3
3

BECKMANN REARRANGEMENT OF KETOXIMES
557
was refluxed for 2 h. After the reaction course, quenched by the addition of H O
2
(10 mL), the organic layer was extracted with ethyl acetate, dried over anhydrous
sodium sulfate, and concentrated under reduced pressure. The resulting crude pro-
duct was purified by silica gel column chromatography to give the corresponding
amide in good yield.
All known compounds gave NMR spectra that matched data reported in the
[13,15]
cited references.
N-Phenylacetamide (2a)
ꢀ
[13]
ꢀ
1
Mp 114–115 C [lit. 114–116 C]; H NMR (400 MHz, CDCl ): d (ppm): 8.59
3
(
2
brs, 1H), 7.53 (d, J ¼ 8.0 Hz, 2H), 7.28 (t, J ¼ 7.7 Hz, 2H), 7.09 (t, J ¼ 7.4 Hz, 1H),
.13 (s, 3H).
N-Phenylbenzamide (2b)
ꢀ
[18]
ꢀ
1
Mp 164–165 C [lit. 164–165 C]; H NMR (400 MHz, CDCl ): d (ppm): 8.03
3
(
7
brs, 1H), 7.87 (d, J ¼ 7.3 Hz, 2H), 7.66 (d, J ¼ 7.9 Hz, 2H), 7.54 (t, J ¼ 7.3 Hz, 1H),
.46 (t, J ¼ 7.5 Hz, 2H), 7.37 (t, J ¼ 7.9 Hz, 2H), 7.16 (t, J ¼ 7.4 Hz, 1H).
N-p-Tolylbenzamide and 4-Methyl-N-phenylbenzamide (2c)
1
H NMR (400 MHz, CDCl ): d (ppm): 7.92–7.73 (m, 6H), 7.65 (d, J ¼ 7.9 Hz,
3
2
(
H), 7.55–7.49 (m, 3H), 7.38 (t, J ¼ 7.8 Hz, 2H), 7.32–7.26 (m, 3H), 7.19–7.14
m, 2H), 2.44 (s, 3H), 2.35 (s, 3H).
4-Chloro-N-p-tolylbenzamide and N-(4-Chlorophenyl)-4-
methylbenzamide (2d)
1
H NMR (400 MHz, DMSO-d ): d (ppm): 10.27 (brs, 1H), 10.21 (brs, 1H), 7.98
6
(
d, J ¼ 8.4 Hz, 2H), 7.87 (d, J ¼ 8.0 Hz, 2H), 7.82 (d, J ¼ 8.7 Hz, 2H), 7.64 (d,
J ¼ 8.2 Hz, 2H), 7.59 (d, J ¼ 8.4 Hz, 2H), 7.39 (d, J ¼ 8.7 Hz, 2H), 7.33 (d, J ¼ 7.9 Hz,
Hz, 2H), 7.15 (d, J ¼ 8.2 Hz, 2H), 2.38 (s, 3H), 2.27 (s, 3H).
4-Methoxy-N-p-tolylbenzamide and N-(4-Methoxyphenyl)-4-
methylbenzamide (2e)
1
H NMR (400 MHz, CDCl ): d (ppm): 8.17 (brs, 1H), 8.16 (brs, 1H), 7.80 (d,
3
J ¼ 8.4 Hz, 2H), 7.74 (d, J ¼ 7.7 Hz, 2H), 7.53 (d, J ¼ 6.3 Hz, 2H), 7.51 (d, J ¼ 5.1 Hz,
2
H), 7.19 (d, J ¼ 7.7 Hz, 2H), 7.11 (d, J ¼ 7.9 Hz, 2H), 6.86 (d, J ¼ 9.6 Hz, 2H), 6.84
(d, J ¼ 9.2 Hz, 2H), 3.85 (s, 3H), 3.78 (s, 3H), 2.38 (s, 3H), 2.32 (s, 3H).
N-(4-Chlorophenyl)-4-methoxybenzamide and 4-Chloro-N-
(4-methoxyphenyl)benzamide (2f)
1
H NMR (400 MHz, DMSO-d ): d (ppm): 10.22 (brs, 1H), 10.20 (brs, 1H), 7.98
6
(d, J ¼ 6.9 Hz, 2H), 7.96 (d, J ¼ 6.7 Hz, 2H), 7.82 (d, J ¼ 8.4 Hz, 2H), 7.68

558
L.-F. LIU ET AL.
(
(
d, J ¼ 8.5 Hz, 2H), 7.58 (d, J ¼ 8.1 Hz, 2H), 7.38 (d, J ¼ 8.4 Hz, 2H), 7.05
d, J ¼ 8.4 Hz, 2H), 6.92 (d, J ¼ 8.6 Hz, 2H), 3.83 (s, 3H), 3.74 (s, 3H).
N-p-Tolylacetamide (2g)
ꢀ
[13]
ꢀ
1
Mp 149–150 C [lit. 149–151 C]; H NMR (400 MHz, CDCl ): d (ppm): 8.28
3
(
(
brs, 1H), 7.40 (d, J ¼ 8.2 Hz, 2H), 7.09 (d, J ¼ 8.1 Hz, 2H), 2.30 (s, 3H), 2.12 (s, 3H).
N-(4-Methoxyphenyl)acetamide (2h)
ꢀ
[13]
ꢀ
1
Mp 128–129 C [lit. 129–130 C]; H NMR (400 MHz, CDCl ): d (ppm): 8.09
3
brs, 1H), 7.38 (d, J ¼ 8.8 Hz, 2H), 6.81 (d, J ¼ 8.5 Hz, 2H), 3.76 (s, 3H), 2.10 (s, 3H).
N-(2-Methoxyphenyl)acetamide (2i)
ꢀ
[13]
ꢀ
1
Mp 85–86 C [lit. 85–86 C]; H NMR (400 MHz, CDCl ): d (ppm): 8.35 (d,
3
J ¼ 7.8 Hz, 1H), 7.79 (brs, 1H), 7.02 (t, J ¼ 7.4 Hz, 1H), 6.94 (t, J ¼ 7.4 Hz, 1H), 6.86
(d, J ¼ 8.0 Hz, 1H), 3.86 (s, 3H), 2.18 (s, 3H).
N-(3-Methoxyphenyl)acetamide (2j)
ꢀ
[13]
ꢀ
87–88 C]; H NMR (400 MHz, CDCl ): d (ppm): 8.58
3
1
Mp 81–82 C [lit.
(
brs, 1H), 7.28 (s, 1H), 7.16 (t, J ¼ 8.1 Hz, 1H), 7.04 (d, J ¼ 7.9 Hz, 1H), 6.64
(d, J ¼ 8.0 Hz, 1H), 3.73 (s, 3H), 2.13 (s, 3H).
N-Phenylpropionamide (2k)
ꢀ
[13]
ꢀ
1
Mp 106–107 C [lit. 103–104 C]; H NMR (400 MHz, CDCl ): d (ppm): 8.30
3
(
2
brs, 1H), 7.55 (d, J ¼ 7.9 Hz, 2H), 7.27 (t, J ¼ 7.7 Hz, 2H), 7.08 (t, J ¼ 7.3 Hz, 1H),
.37 (q, J ¼ 7.5 Hz, 2H), 1.21 (t, J ¼ 7.6 Hz, 3H).
N-(4-Chlorophenyl)acetamide (2l)
ꢀ
[19]
ꢀ
1
Mp 180–181 C [lit. 180 C]; H NMR (400 MHz, DMSO-d ): d (ppm): 10.05
6
(
(
brs, 1H), 7.60 (d, J ¼ 8.5 Hz, 2H), 7.32 (d, J ¼ 8.5 Hz, 2H), 2.04 (s, 3H).
Azacyclotridecan-2-one (2m)
ꢀ
[20]
ꢀ
1
Mp 150–151 C [lit. 143–145 C]; H NMR (400 MHz, CDCl ): d (ppm): 6.07
3
brs, 1H), 3.26 (dd, J ¼ 5.7, 10.5 Hz, 2H), 2.19–2.16 (m, 2H), 1.68–1.62 (m, 2H),
1
.55–1.45 (m, 2H), 1.34–1.27 (m, 14H).
ACKNOWLEDGMENTS
This work was supported by the Natural Science Foundation of China
No. NSFC 20602011), New Century Excellent Talents in University, the Ministry
(
of Education, China (No. NCET-07–0283), and the ‘‘111’’ Project (No. B07023).

BECKMANN REARRANGEMENT OF KETOXIMES
559
REFERENCES
1
. K u¨ rti, L.; Czak o´ , B. Strategic Applications of Named Reactions in Organic Synthesis;
Elsevier Academic Press: New York, 2005.
2
. (a) Li, W.-C.; Lu, A.-H.; Palkovits, R.; Schmidt, W.; Spliethoff, B.; Schuth, F. Hierarchi-
cally structured monolithic silicalite-1 consisting of crystallized nanoparticles and its
performance in the Beckmann rearrangement of cyclohexanone oxime. J. Am. Chem.
Soc. 2005, 127, 12595–12600; (b) Dahlhoff, G.; Niederer, J. P. M.; Hoelderich, W. F.
e-Caprolactam: New by-product free synthesis routes. Cat. Rev. Sci. Eng. 2001, 43, 381.
. (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Beckmann rearrangement of oximes under
very mild conditions. J. Org. Chem. 2002, 67, 6272–6274; (b) Wang, B.; Gu, Y.; Luo, C.;
Yang, T.; Yang, L.; Suo, J. Sulfamic acid as a cost-effective and recyclable catalyst for
liquid Beckmann rearrangement, a green process to produce amides from ketoximes
without waste. Tetrahedron Lett. 2004, 45, 3369–3372.
3
4
5
. (a) Ghiaci, M.; Abbaspur, A.; Kalbasi, R. J. Vapor-phase Beckmann rearrangement of
cyclohexanone oxime over H PO =ZrO -TiO . Appl. Catal. A 2005, 287, 83–88; (b) Forni,
3
4
2
2
L.; Fornasari, G.; Giordano, G.; Lucarelli, C.; Katovic, A.; Trifiro, F.; Perri, C.; Nagy, J.
B. Vapor-phase Beckmann rearrangement using high silica zeolite catalyst. Phys. Chem.
Chem. Phys. 2004, 6, 1842–1847.
. (a) Ikushima, Y.; Hatakeda, K.; Sato, M.; Sato, O.; Arai, M. Innovation in a chemical
reaction process using a supercritical water microreaction system: Environmentally
friendly production of e-caprolactam. Chem. Commun. 2002, 2208–2209; (b) Boero, M.;
Ikeshoji, T.; Liew, C. C.; Terakura, K.; Parrinello, M. Hydrogen bond–driven chemical
reactions: Beckmann rearrangement of cyclohexanone oxime into e-caprolactam in super-
critical water. J. Am. Chem. Soc. 2004, 126, 6280–6286.
6
. (a) Zicmanis, A.; Katkevica, S.; Mekss, P. Lewis acid–catalyzed Beckmann rearrangement
of ketoximes in ionic liquids. Catal. Commun. 2009, 10, 614–619; (b) Guo, S.; Deng, Y. Q.
Environmentally friendly Beckmann rearrangement of oximes catalyzed by metaboric
acid in ionic liquids. Catal. Commun. 2005, 6, 225–228.
7
8
9
. Arisawa, M.; Yamaguchi, M. Rhodium-catalyzed Beckmann rearrangement. Org. Lett.
2001, 3, 311–312.
. Yadav, J. S.; Reddy, B. V. S.; Madhavi, A. V.; Ganesh, Y. S. S. Yb(OTf)
3
-catalysed facile
conversion of ketoximes to amides and lactams. J. Chem. Res., Synop. 2002, 236–238.
. De, S. K. Facile Beckmann rearrangement of ketoximes mediated by yttrium triflate. Org.
Prep. Proced. Int. 2004, 36, 383–386.
1
1
1
1
1
0. Yan, P.; Batamack, P.; Prakash, G. K. S.; Olah, G. A. Gallium(III) triflate – catalyzed
Beckmann rearrangement. Catal. Lett. 2005, 103, 165–168.
1. De, S. K. Nd(OTf)
Synop. 2004, 131–132.
2. De, S. K. RuCl -catalyzed facile conversion of arylalkyl ketoximes to amides. Synth.
3
-mediated facile conversion of ketoximes to amides. J. Chem. Res.,
3
Commun. 2004, 34, 3431–3434.
3. Ramalingan, C.; Park, Y. T. Mercury-catalyzed rearrangement of ketoximes into amides
and lactams in acetonitrile. J. Org. Chem. 2007, 72, 4536–4538.
4. (a) Ghiaci, M.; Imanzadeh, G. H. A facile Beckmann rearrangement of oximes with AlCl
3
in the solid state. Synth. Commun. 1998, 28, 2275–2280; (b) Moghaddam, F. M.; Rad, A.
A. R.; Hassan, Z.-B. Solid-supported microwave-assisted Beckmann rearrangement of
ketoximes in dry media. Synth. Commun. 2004, 34, 2071–2075; (c) Torisawa, Y.; Nishi,
T.; Minamikawa, J. A study on the conversion of indanones into carbostyrils. Biorg.
Med. Chem. 2003, 11, 2205–2209; (d) Lee, B. S.; Chi, D. Y. Beckmann rearrangement
of 1-indanone oxime using aluminum chloride. Bull. Korean Chem. Soc. 1998, 19,
1373–1375.

560
L.-F. LIU ET AL.
15. (a) Pi, H. J.; Dong, J. D.; An, N.; Du, W. T.; Deng, W. P. Unexpected results from the
re-investigation of the Beckmann rearrangement of ketoximes into amides by using TsCl.
Tetrahedron 2009, 65, 7790–7793; (b) Kakuta, H.; Zheng, X.; Oda, H.; Harada, S.;
Sugimoto, Y.; Sasaki, K.; Tai, A. J. Med. Chem. 2008, 51, 2400–2411; (c) Ockey, D.
A.; Dotson, J. L.; Struble, M. E.; Stults, J. T.; Bourell, J. H.; Clark, K. R.; Gadek, T.
R. Bioorg. Med. Chem. 2004, 12, 37–44; (d) Han, K.-J.; Tae, B. S.; Kim, M. Org. Prep.
Proced. Int. 2005, 37, 198–203; (e) Kozuka, S.; Takahashi, H.; Oae, S. Bull. Chem. Soc.
Jpn. 1971, 44, 1965–1966.
1
6. Zhu, M. Z.; Cha, C. T.; Deng, W. P.; Shi, X. X. A mild and efficient catalyst for the
Beckmann rearrangement, BOP-Cl. Tetrahedron Lett. 2006, 47, 4861–4863.
7. (a) Zhu, M. Studies on small-molecule catalyzed Beckmann rearrangement. M. S. thesis,
East China University of Science and Technology, Shanghai, China, 2007; (b) Hashimoto,
M.; Obora, Y.; Sakaguchi, S.; Ishii, Y. Beckmann rearrangement of ketoximes to lactams
by triphosphazene catalyst. J. Org. Chem. 2008, 73, 2894–2897.
1
1
8. Sardarian, A. R.; Shahsavari-Fard, Z.; Shahsavari, H. R.; Ebrahimi, Z. Efficient
Beckmann rearrangement and dehydration of oximes via phosphonate intermediates.
Tetrahedron Lett. 2007, 48, 2639–2643.
1
2
9. Zhang, Y.; Zhang, Y. One-pot reductive conversion of nitroarenes to N-arylacetamides
mediated by metallic samarium. J. Chem. Res. 2004, 596–598.
0. Yadav, J. S.; Reddy, B. V. S.; Reddy, U. V. S.; Praneeth, K. Azido-Schmidt reaction for
the formation of amides, imides, and lactams from ketones in the presence of FeCl3.
Tetrahedron Lett. 2008, 49, 4742–4745.