3-methyl-4-oxa-5-azahomoadamantane as an organocatalyst for the aerobic oxidation of primary amines to oximes in water

Article abstract of DOI:10.1002/adsc.201400601

A simple and efficient catalytic system for the aerobic oxidation of primary amines into corresponding oximes has been developed, with 3-methyl-4-oxa-5-azahomoadamantane as catalyst, acetaldoxime as co-catalyst and water as solvent. This process, which uses oxygen (O₂) as an economic and green oxidant and water as a green solvent, tolerates a wide range of substrates, affording the target oximes in moderate to excellent yields. It was found that high selectivity was achieved when 3-methyl-4-oxa-5-azahomoadamantane was used, and E-type oximes were the only detected products. A possible mechanism for this catalytic process is proposed.

Full text of DOI:10.1002/adsc.201400601

COMMUNICATIONS
DOI: 10.1002/adsc.201400601
3-Methyl-4-oxa-5-azahomoadamantane as an Organocatalyst for
the Aerobic Oxidation of Primary Amines to Oximes in Water
Jiatao Yu,a Yong Jin,a and Ming Lua,*
a
Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, Peoples Republic China
Fax : (+86)-025-8431-5030; phone: (+86)-025-8430-3298; e-mail: luming302@126.com
Received: June 20, 2014; Revised: November 27, 2014; Published online: && &&, 0000
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201400601.
Abstract: A simple and efficient catalytic system
for the aerobic oxidation of primary amines into
corresponding oximes has been developed, with 3-
methyl-4-oxa-5-azahomoadamantane as catalyst,
acetaldoxime as co-catalyst and water as solvent.
This process, which uses oxygen (O2) as an econom-
ic and green oxidant and water as a green solvent,
tolerates a wide range of substrates, affording the
target oximes in moderate to excellent yields. It was
found that high selectivity was achieved when 3-
methyl-4-oxa-5-azahomoadamantane was used, and
E-type oximes were the only detected products. A
possible mechanism for this catalytic process is pro-
posed.
hydroxylACTHNGUTERNNUaG mine salt relative to the respective sub-
strates, (ii) an equal mol equivalent of base should be
used relative to the hydroxylamine salt, (iii) large
amounts of by-products are generated during the oxi-
mation reaction, (iv) yields of the oximes are relative-
ly low because the resulting oximes can undergo
either dehydration to nitriles or acid-catalyzed Beck-
mann rearrangement to amides.
Recently, some studies have been performed to
obtain oximes via the aerobic oxidation of primary
amines by employing 1,1-diphenyl-2-picrylhydrazyl
(DPPH) and tungsten-alumina (WO3/Al2O3) as cata-
lyst.[14] (Scheme 1). Nonetheless, this method suffers
from some limitations: (i) it is only applicable for ali-
phatic primary amines, (ii) it requires metal com-
pounds or organic solvent. Therefore, it is of signifi-
cant importance to develop a mild, convenient and ef-
ficient method that can suppress the formation of by-
products and increase the yields of the corresponding
oximes.
Keywords: aerobic oxidation; amines; 3-methyl-4-
oxa-5-azahomoadamantane; oximes; water
Due to their unique behavior and eminent reactivi-
Oximes have been widely utilized in medicine, indus- ty, nitrogen oxides (such as TEMPO, NHPI and
try, and analytical chemistry, and they are also widely THICA) have drawn considerable attention in the
used as intermediates in the synthesis of commodity
products, fine chemicals, medicines, and biologically
active compounds.[1–5] Moreover, oximes are valuable
synthetic tools, which can be either reduced to amines
or oxidized to nitrile oxides,[6,7] and they can also be
dehydrated to nitriles or undergo an acid-catalyzed
Beckmann rearrangement to afford amides.[8] Further-
more, oximes are very important ligands in the forma-
tion of mono- and polynuclear metal complexes.[9] In
addition, oximes are highly crystalline compounds
that find applications not only for protection, but also
for purification and characterization of carbonyl com-
pounds.[10,11] The traditional way to obtain oximes is
the reaction of a carbonyl compound with hydroxyl-
ACHTUNGTRENNUNGamine hydrochloride in the presence of a stoichiomet-
ric amount of base.[12,13] However, this method has
some drawbacks that restrict its further application:
Scheme 1. The aerobic oxidation of primary amines cata-
lyzed by 3-methyl-4-oxa-5-azahomoadamantane/acetaldox-
(i) the cost of stoichiometric or excess amounts of ime.
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1
ÞÞ
These are not the final page numbers!

COMMUNICATIONS
Jiatao Yu et al.
Table 1. Oxidation of the benzylamine under various conditions.[a,b]
Entry
Catalyst (mol%)
Co-catalyst (mol%)
Solvent
Temperature [oC]
Gas
Yield[b] [%] (E/Z)
1
2
3
4
5
6
7
8
A (2.5)
THICA (2.5)
NHPI (2.5)
TEMPO (2.5)
A (2.5)
A (2.5)
A (2.5)
A (2.5)
A (2.5)
A (2.5)
A (2.5)
A (2.5)
A (2.5)
A (2.5)
A (2.5)
A (5)
A (1)
A (0.5)
A (0)
A (1)
A (1)
A (1)
A (1)
A (1)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetoxime (10)
H2O
H2O
H2O
H2O
H2O
H2O
H2O
DMSO
DMF
EtOH
MeCN
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
refluxing
refluxing
refluxing
refluxing
refluxing
refluxing
refluxing
refluxing
refluxing
refluxing
refluxing
80
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
O2
air
N2
92/0
76/4
50/11
45/8
81/0
76/0
71/0
–
dimethylglyoxime (10)
cyclohexanone oxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (10)
acetaldoxime (0)
acetaldoxime (5)
acetaldoxime (20)
acetaldoxime (10)
acetaldoxime (10)
9
–
–
–
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
84/0
63/0
36/0
trace
92/0
92/0
83/0
trace
trace
80/0
92/0
79/0
trace
60
40
r.t.
refluxing
refluxing
refluxing
refluxing
refluxing
refluxing
refluxing
refluxing
refluxing
[a]
Reaction conditions: 1 mmol benzylamine was dissolved in 5 mL solvent. The catalyst and co-catalyst were then added,
and the mixture stirred for 24 h under different gas atmosphere at different temperatures.
The reported yields were determined by H NMR.
[b]
1
aerobic oxidation of hydrocarbons, alcohols, and strates, affording the target oximes in moderate to ex-
amines over the last decade.[15] Recently, 3-methyl-4- cellent yields.
oxa-5-azahomoadamantane,[16] which is a novel al-
As a representative example, the aerobic oxidation
koxyamine-type organocatalyst, was found to enable of benzylamine (Scheme 1) was selected to optimize
the highly efficient oxidation of primary and secon- the reaction conditions (Table 1). It is pleasing that
dary alcohols into the corresponding carbonyl com- the oxidation of benzylamine with O2 (1 atm) cata-
pounds using NaOCl as the terminal oxidant. Based lyzed
by
3-methyl-4-oxa-5-azahomoadamantane
on this work, we tried to extend the application of (2.5 mol%) combined with acetaldoxime (10 mol%)
this alkoxyamine-type organocatalyst for other oxida- gave solely (E) benzaldoxime in 92% yield (Table 1,
tions.
Herein, we report a novel, efficient and metal-free Unsatisfactorily, when THICA (N’,N’’,N’’’-trihydroxy-
approach for the aerobic oxidation of primary amines isocyanuric acid), NHPI (-hydroxyphthalimide), and
entry 1). Other nitrogen oxides were also examined.
AHCTUNGTRENNUNG
into the corresponding oximes. This process with 3- TEMPO (2,2,6,6-tetramethylpiperidine 1-oxyl) were
methyl-4-oxa-5-azahomoadamantane as catalyst, ace- used, the reaction proceeded in low yield, and the (Z)
1
taldoxime as co-catalyst, O2 as the terminal oxidant, benzaldoxime was detected by H NMR (entries 2–4).
and water as solvent, tolerates a wide range of sub- Several acetaldoxime analogues were compared (en-
2
asc.wiley-vch.de
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 0000, 000, 0 – 0
ÝÝ
These are not the final page numbers!

COMMUNICATIONS
3-Methyl-4-oxa-5-azahomoadamantane as an Organocatalyst
Table 2. The aerobic oxidation of primary amines into oximes catalyzed by 3-methyl-4-oxa-5-azahomoadaman-
tane and
acetaldoxime.[a,b]
[a]
Reaction conditions: 1 mmol primary amine, 1 mol% 3-methyl-4-oxa-5-azahomoadamantane and 10 mol%
acetaldoxime was dissolved in 5 mL H2O, and the mixture was stirred for several hours under O2 atmosphere
at refluxing temperature.
The reported yields were determined by H NMR.
[b]
1
tries 5–7). Substitution by acetoxime, dimethylglyox- 3-methyl-4-oxa-5-azahomoadamantane could not
ime, or cyclohexanone oxime led to lower yields. form its radical in these solvents (entries 1, 8–11). Re-
Screening of different solvents revealed that the sol- ducing the reaction temperature from refluxing condi-
vent played an important role in this reaction. Nota- tions to room temperature led to great decrease in
bly, H2O was the only effective solvent, benzaldoxime the yields (entries 1, 12–15). Subsequently, the
could not form in other solvents such as DMSO, amount of the catalyst was screened. And the result
DMF, EtOH, MeCN, which may because the catalyst showed that the optimum amount of acetaldoxime
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
3
ÞÞ
These are not the final page numbers!

COMMUNICATIONS
Jiatao Yu et al.
was 10 mol% and 1 mol% for 3-methyl-4-oxa-5-aza-
homoadamantane (entries 1, 16–22). Besides, when
using air in the reaction, the yield was reduced slight-
ly (entries 17 and 23). Also the reaction could not be
conducted under an N2 atmosphere (entry 24).
Next, the substrate scope for the aerobic oxidation
of the primary amines was examined in detail under
the optimized reaction conditions. As shown in
Table 2, the reaction could be successfully applied to
a range of different substituted benzylamines and
gave the corresponding (E) products in moderate to
excellent yields, with no (Z) products formed. The
above results indicated that the catalytic oximation of
benzylamines with electron-withdrawing substituents
Scheme 2. The aerobic oxidation of benzylamine to oxime
catalyzed by 3-methyl-4-oxa-5-azahomoadamantane/acetal-
doxime.
gave excellent yields except for the halo-substituted erated were undertaken. The aerobic oxidation of
benzylamines (Table 2, entries b–d, i). In the case of benzylamine (10 mmol) catalyzed by 3-methyl-4-oxa-
benzylamines with electron-donating groups, good 5-azahomoadamantane (0.1 mmol) and acetaldoxime
yields in the range 85–93% could be achieved (entries (1 mmol) in water was performed at refluxing condi-
e–h, n). When the benzylamines bear the same sub- tions. After cooling to room temperature, a residue
stituent, the oxime yields from the ortho or meta sub- was obtained after extraction and evaporation. Then
stituted compounds are lower than that for para sub- the crude product was purified by chromatography to
stitution (entries c, g, i, l). This should be attributed give the product (E-benzaldoxime) in 92% yield and
to the steric hindrance effect. Fortunately, 1-naphtha- 1-Me-AZADO (1-methyl-2-azaadamntane N-oxyl,
lenemethylamine, 9-anthracenemethylamine and 3- the data of which are available in the Supporting In-
phenyl-2-propyleneamine could also be successfully formation) in 56% (based on the equiv. of 3-methyl-4-
converted into the corresponding oximes in good oxa-5-azahomoadamantane) yield (Scheme 2).
yields in this catalytic system (entries o–q). Moreover,
Based on these results and previous literature re-
we also subjected heterocyclic primary amines to the ports,[15,16,18] a possible catalytic mechanism of 3-
employed reaction conditions. To our surprise, hetero- methyl-4-oxa-5-azahomoadamantane/acetaldoxime in
cyclic amines showed high reactivity to give the corre- the aerobic oxidation of primary amines was proposed
sponding oximes in good yields (entries r–y). This cat- as shown in Scheme 3. The first step of the reaction
alytic system was then applied to the oxidation of ali- lies in the generation of the corresponding N-oxyl
phatic amines to further extend the substrate scope. radical of acetaldoxime, through reaction of acetal-
Unfortunately, merely a trace amount of octanal doxime and dioxygen. And then this N-oxyl radical
oxime was detected when octylamine was exposed to abstracts hydrogen from 3-methyl-4-oxa-5-azahomo-
this catalytic system for 24 h (entry z). The reason
ACHTUNGTRENaNGNU damantane 1 to recover the acetaldoxime. Simulta-
may be that the electron-withdrawing effect of the ar- neously, 1 is converted to its radical 2. The rearrange-
À
omatic base was stronger than that of the aliphatic ment of 2 gives the N O radical species 3 (1-Me-
one, when the electron-withdrawing ability of the AZADO). Radical 3 abstracts a hydrogen atom from
groups on the a carbon atom was stronger, the reac- the primary amine to form an a-aminobenzyl radical
tion proceeded more easily. Secondary amines and and was transformed to 4 at the same time. Then the
aniline type substrates [such as dibenzylamine and a-aminobenzyl radical was readily captured by O2 to
aniline (not shown)] were not oxidized under this cat- give the a-aminobenzylperoxy radical, which under-
alytic system.
went abstraction of hydrogen from 4 to give the a-
Some preliminary mechanistic studies of the reac- aminobenzyl hydroperoxide. And 4 was then convert-
tion were also conducted. Control experiments ed to form 3 again to establish the catalytic cycle. Fi-
showed that no product appeared in the presence of nally, the a-aminobenzyl hydroperoxide was dehy-
3-methyl-4-oxa-5-azahomoadamantane or acetaldox- drated to form the desired product. After analyzing
ime alone (Table 1, entries 19 and 20). When the reac- the isolated products by 1H NMR, E-type oximes
tion was conducted under an N2 atmosphere, only were obtained as the only products.
a trace amount of product was obtained (Table 1,
In conclusion, we have developed a simple, efficient
entry 24). Thus, acetaldoxime, 3-methyl-4-oxa-5-aza- and green catalytic system consisting of 3-methyl-4-
homoadamantane and O2 were essential for this reac- oxa-5-azahomoadamantane and acetaldoxime for the
tion.
aerobic oxidative synthesis of oximes from primary
Besides, in order to obtain mechanistic insight into amines. This practical reaction with O2 as green and
the 3-methyl-4-oxa-5-azahomoadamantane-catalyzed economic oxidant and water as green solvent, toler-
oxidation, attempts to identify the active species gen- ates a wide range of substrates, affording the target
4
asc.wiley-vch.de
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 0000, 000, 0 – 0
ÝÝ
These are not the final page numbers!

COMMUNICATIONS
3-Methyl-4-oxa-5-azahomoadamantane as an Organocatalyst
Scheme 3. The possible reaction mechanism of the aerobic oxidation catalyzed by 3-methyl-4-oxa-5-azahomoadamantane
and acetaldoxime.
oximes in moderate to excellent yields. Besides, 3-
methyl-4-oxa-5-azahomoadamantane showed excel-
lent selectivity as oxidant for the primary amines, and
E-type oximes were obtained as the only products.
Furthermore, a plausible reaction mechanism was
proposed based on the experimental observations and
literature precedents.
Experimental Section
General Remarks
All starting materials were purchased from commercial sour-
ces and used without further treatment. All known com-
pounds were identified by appropriate techniques and com-
pared with previously reported data. NMR (500 MHz) spec-
Scheme 4. The preparation of the 3-methyl-4-oxa-5-azaho-
moadamantane.
tra were recorded on a Bruker 500 spectrometer with tetra-
methylsilane (TMS) as an internal standard. Mass spectra
were recorded on an Agilent Technologies 6110 quadrupole
MS equipped with electrospray ionization (ESI) probe oper-
ating in positive/negative ion mode. Analytical thin layer
chromatography (TLC) was performed on precoated silica
gel 60 F254 plates. Yields refer to the isolated yields of the
products after purification by silica-gel column chromatogra-
phy (300 mesh). All the analytical data and spectra are
available in the Supporting Information.
bled into the flask at a flow rate of 20 mLminÀ1. The reac-
tion mixture was stirred at refluxing conditions for several
hours and the reaction progress was monitored by TLC.
After completion, the final reaction mixture was cooled to
room temperature and extracted with ether. The organic
layer was washed with brine, dried over MgSO4 and concen-
trated under reduced pressure. When necessary, the crude
product was purified by chromatography with ethyl acetate/
petroleum ether (1:8) as eluent.
Preparation of the 3-Methyl-4-oxa-5-azahomo-
adamantane
3-Methyl-4-oxa-5-azahomoadamantane was prepared by the
literature procedure[16,17] as shown in Scheme 4. The detailed
procedure is available in the Supporting Information.
1H NMR (500 MHz, CDCl3): d=4.68 (br s, 1H), 3.58 (s,
1H), 2.07–1.97 (m, 2H), 1.95–1.68 (m, 8H), 1.61–1.47 (m,
2H), 1.23 (s, 3H); 13C NMR (125.72 MHz, CDCl3): d=80.7,
55.0, 42.0, 36.8, 34.3, 29.8, 26.3; MS: m/z=168 (M+).
References
[1] G. M. Robertoson, in: Comprehensive Functional
Group Transformation, (Eds.: A. R. Katritzky, O.
Meth-Cohn, C. W. Rees), Elsevier, Oxford, 1995, vol. 3,
pp 425.
[2] a) H. Iwamura, J. Med. Chem. 1980, 23, 308–312; b) Y.
Takahashi, Y. Miyashita, Y. Tanaka, H. Abe, S. Sasaki,
J. Med. Chem. 1982, 25, 1245–1248.
General Procedure for the Synthesis of Oximes
A mixture of 1 mmol primary amine, 1 mol% 3-methyl-4-
oxa-5-azahomoadamantane, 10 mol% acetaldoxime and
5 mL H2O was placed into a three-necked flask. O2 was bub-
[3] P. A. Eyer, F. Worek, in: Chemical Warfare Agents:
Toxicology and Treatment, (Eds.: T. C. Marrs, R. L.
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
5
ÞÞ
These are not the final page numbers!

COMMUNICATIONS
Jiatao Yu et al.
Maynard, F. R. Sidell), Wiley, Chichester, 2007, pp 305–
329.
[10] R. P. Frutos, D. M. Spero, Tetrahedron Lett. 1998, 39,
2475–2478.
[11] a) S. Sasatani, T. Miyazak, K. Maruoka, H. Yamamoto,
Tetrahedron Lett. 1983, 24, 4711–4712; b) S. Negi, M.
Matsukura, M. Mizuno, K. Miyake, Synthesis 1996,
991–996.
[12] A. Pohjakallio, P. M. Pihko, Chem. Eur. J. 2009, 15,
3960–3964.
[13] C. L. Allen, S. Davulcu, J. M. J. Williams, Org. Lett.
2010, 12, 5096–5099.
[4] a) A. Atria, M. Michael, Pharmazie 1982, 37, 551–553;
b) A. Nakayama, H. Iwamura, A. Niwa, Y. Nakagawa,
T. Fujita, J. Agric. Food Chem. 1985, 33, 1034–1041;
c) J. P. Ley, H. J. Bertram, Eur. J. Lipid Sci. Technol.
2002, 104, 319–323; d) M. Kato, S. Nishino, M. Ohno, S.
Fukuyama, Y. Kita, Y. Hirasawa, Y. Nakanishi, H. Ta-
kasugi, K. Sakane, Bioorg. Med. Chem. Lett. 1996, 6,
33–38.
[5] R. W. Hartmann, M. Hector, S. Haidar, P. B. Ehmer, W.
Reichert, J. Jose, J. Med. Chem. 2000, 43, 4266–4277.
[6] B. A. Mendelsohn, S. Lee, S. Kim, F. Teyssier, V. S.
Aulakh, M. A. Ciufolini, Org. Lett. 2009, 11, 1539–1542.
[7] N. A. Owston, A. J. Parker, J. M. J. Williams, Org. Lett.
2007, 9, 3599–3601.
[8] a) T. Shono, Y. Matsumura, K. Tsubata, T. Kamada, K.
Kishi, J. Org. Chem. 1989, 54, 2249–2251; b) S. H. Yang,
S. Chang, Org. Lett. 2001, 3, 4209–4211; c) K. Yamagu-
chi, H. Fujiwara, Y. Ogasawara, M. Kotani, N. Mizuno,
Angew. Chem. 2007, 119, 3996–3999; Angew. Chem.
Int. Ed. 2007, 46, 3922–3925; d) N. A. Owston, A. J.
Parker, J. M. J. Williams, Org. Lett. 2007, 9, 3599–3601;
e) H. Fujiwara, Y. Ogasawara, K. Yamaguchi, N.
Mizuno, Angew. Chem. 2007, 119, 5294–5297; Angew.
Chem. Int. Ed. 2007, 46, 5202–5205.
[9] a) P. Chaudhuri, Coord. Chem. Rev. 2003, 243, 143–190;
b) V. Y. Kukushikin, A. J. L. Pombeiro, Coord. Chem.
Rev. 1999, 181, 147–175; c) V. Y. Kukushikin, D.
Tudela, A. J. L. Pombeiro, Coord. Chem. Rev. 1996,
156, 333–362.
[14] K. Suzuki, T. Watanabe, S.-I. Murahashi, J. Org. Chem.
2013, 78, 2301–2310.
[15] a) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal.
2001, 343, 393–427; b) F. Recupero, C. Punta, Chem.
Rev. 2007, 107, 3800–3842; c) R. A. Sheldon, I. W. C. E.
Arends, Adv. Synth. Catal. 2004, 346, 1051–1071;
d) R. A. Sheldon, I. W. C. E. Arends, G.-J. Brink, A.
Dijksman, Acc. Chem. Res. 2002, 35, 774–781; e) C.
Galli, P. Gentili, O. Lanzalunga, Angew. Chem. 2008,
120, 4868–4874; Angew. Chem. Int. Ed. 2008, 47, 4790–
4796; f) T. Vogler, A. Studer, Synthesis 2008, 1979–
1993; g) Y.-X. Chen, L.-F. Qian, B. Han, Angew. Chem.
2008, 120, 9470–9473; Angew. Chem. Int. Ed. 2008, 47,
9330–9333.
[16] Y. Sasano, K. Murakami, T. Nishiyama, E. Kwon, Y.
Iwabuchi, Angew. Chem. 2013, 125, 12856–12859;
Angew. Chem. Int. Ed. 2013, 52, 12624–12627.
[17] M. Shibuya, M. Tomizawa, I. Suzuki, Y. Iwabuchi, J.
Am. Chem. Soc. 2006, 128, 8412–8413.
[18] K. Suzuki, T. Watanabe, S.-I. Murahashi, Angew. Chem.
2008, 120, 2109–2111; Angew. Chem. Int. Ed. 2008, 47,
2079–2081.
6
asc.wiley-vch.de
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 0000, 000, 0 – 0
ÝÝ
These are not the final page numbers!

COMMUNICATIONS
3-Methyl-4-oxa-5-azahomoadamantane as an Organocatalyst
for the Aerobic Oxidation of Primary Amines to Oximes in
Water
7
Adv. Synth. Catal. 2015, 357, 1 – 7
Jiatao Yu, Yong Jin, Ming Lu*
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
7
ÞÞ
These are not the final page numbers!