Simple synthesis of N-alkoxymethyl derivatives of anilides

Article abstract of DOI:10.1081/SCC-100105679

Facile, two-step synthesis of N-alkoxymethyl derivatives of anilides consisting of the methoxymethylation of the appropriate anilides with chlomethyl methyl ether followed by heating with an alcohol in the presence of an acid is described.

Full text of DOI:10.1081/SCC-100105679

This article was downloaded by: [University of Nebraska, Lincoln]
On: 10 June 2013, At: 11:07
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
SIMPLE SYNTHESIS OF N-ALKOXYMETHYL DERIVATIVES
OF ANILIDES
Witold Danikiewicz a & Rafal Szmigielski a
a Polish Academy of Sciences, ul. Kasprzaka 44/52, Institute of Organic Chemistry, P.O.
Box 58, Warszawa 42, 01-224, Poland
Published online: 16 Aug 2006.
To cite this article: Witold Danikiewicz & Rafal Szmigielski (2001): SIMPLE SYNTHESIS OF N-ALKOXYMETHYL DERIVATIVES
OF ANILIDES, Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic
Chemistry, 31:19, 3047-3054
To link to this article: http://dx.doi.org/10.1081/SCC-100105679
PLEASE SCROLL DOWN FOR ARTICLE
Full terms and conditions of use: http://www.tandfonline.com/page/terms-and-conditions
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.
The publisher does not give any warranty express or implied or make any representation that the contents
will be complete or accurate or up to date. The accuracy of any instructions, formulae, and drug doses
should be independently verified with primary sources. The publisher shall not be liable for any loss, actions,
claims, proceedings, demand, or costs or damages whatsoever or howsoever caused arising directly or
indirectly in connection with or arising out of the use of this material.

SYNTHETIC COMMUNICATIONS, 31(19), 3047–3054 (2001)
SIMPLE SYNTHESIS OF
N-ALKOXYMETHYL DERIVATIVES
OF ANILIDES
Witold Danikiewicz* and Rafal Szmigielski
Institute of Organic Chemistry,
Polish Academy of Sciences, ul. Kasprzaka 44/52,
01-224 Warszawa 42, P.O. Box 58, Poland
ABSTRACT
Facile, two-step synthesis of N-alkoxymethyl derivatives of
anilides consisting of the methoxymethylation of the appro-
priate anilides with chlomethyl methyl ether followed by heat-
ing with an alcohol in the presence of an acid is described.
N-Alkoxymethyl derivatives of anilides (1) are compounds of consi-
derable interest due to their herbicidal activity. An important group of
them are N-(alkoxymethyl)-2-chloroacetanilide derivatives, e.g. AlachlorÕ
(1, R1¼CH2Cl, R2¼CH3, R3¼R4¼C2H5), which are manufactured as com-
mercial herbicides on the large scale.1–4
There are a few methods of synthesis of this type of compounds.
Usually, they are prepared in several steps starting from the appropriate
anilines and aldehydes.5,6 This type of reactions involves N-acyliminium
salt intermediate, which is not easy for operating. Another competitive
*Corresponding author. E-mail: witold@icho.edu.pl
3047
Copyright & 2001 by Marcel Dekker, Inc.
www.dekker.com

ORDER
REPRINTS
3048
DANIKIEWICZ AND SZMIGIELSKI
method for the synthesis of these compounds consists of the alkylation with
the corresponding alkoxymethyl chlorides.7 However, preparation of the
alkoxymethyl chlorides by the method described by Wedekind is difficult
and inconvenient.8
In the present paper we would like to report a simple, two step syn-
thesis of N-alkoxymethyl derivatives of acetanilide, formanilide and benza-
nilide. In the first step N-(methoxymethyl)anilides are prepared from the
corresponding anilides by the action of methoxymethyl chloride under Phase
Transfer Catalysis (PTC) conditions in the presence of the solid base and
catalytic amount of tetraalkylammonium salt. Alternatively, tert-BuOK-
THF system can be used for alkylation. The second step consists of the
heating up the N-(methoxymethyl)-anilides with an excess of the aliphatic
alcohols with catalytic amount of p-toluenesulfonic acid (Scheme 1).
Scheme 1.
Although the procedure of methoxymethylation of the amidic nitrogen
atom with methoxymethyl chloride in the presence of 50% NaOHaq and the
appropriate PTC catalyst has been applied many times7,9 there is no evidence
of carrying out such reaction in PTC system with the solid base. In the course
of the present work we have checked a few bases and solvents. It turned out

ORDER
REPRINTS
N-ALKOXYMETHYL DERIVATIVES
3049
that for N-methoxymethylation reaction of acetanilide and formanilide
powdered KOH in DMSO in the presence of catalytic amount of tetra-
butylammonium hydrogensulfate gave the best results. In the case of
benzanilide, however, tert-BuOK solution in THF appeared to give the
highest yield.
N-Methoxymethyl compounds (i.e. N,O-acetals) are known to pro-
duce iminium cations under acidic conditions.10 In the presence of the
nucleophile, generated iminium cation can be trapped to afford many inter-
esting organic compounds, as it was presented in the syntheses of tetra-
hydroquinolines and julolidines.11 There are no papers dealing with the
reaction of N-methoxymethylated amides with alcohols as nucleophiles in
acidic conditions. Only Villiger12 and Muzic13 during their investigations of
the properties of N-alkoxymethyl N,N-dialkylamines stated that the course
of discussed transformation is possible, although without any experimental
details. It prompted us to study carefully this type of useful reaction espe-
cially in relation to compounds 1. It’s clear that this reaction can be applied
to other similar compounds e.g. AlachlorÕ derivatives.
According to our method, N-(methoxymethyl)anilides are heated with
an excess of the aliphatic alcohol for 1–4 h in the presence of p-toluene-
sulfonic acid to give various N-(alkoxymethyl)anilides in good yields
(Table 1). It is obvious that the scope of this reaction is much broader
and gives an easy access to many interesting compounds.
Surprisingly, we have found that unlike other performed reactions,
N-(methoxymethyl)acetanilide reacts with cyclohexanol at 60ꢀC in the pre-
sence of the catalytic amount of p-TsOH to give an equimolar mixture
of acetanilide and bis(cyclohexyloxy)methane instead of the expected
Table 1. Preparation of N-Alkoxymethylanilides from the Appropriate
N-Methoxymethylanilides
Product
R1
R2
T (ꢀC)
t (h)
Yield (%)
5b
5c
5d
5e
5f
5g
5h
5i
Me
Me
Me
Me
Me
Me
Me
Me
H
Et
n-Pr
Ipr
n-Bu
IBu
sec-Bu
tert-Bu
78
60
82
75
80
85
60
r.t.
78
78
1.5
1
1.5
3
4
3
2
24
3
92
90
83
70
74
90
60
81
67
93
CH2CH ¼ CH2
6b
7b
Et
Et
Ph
2.5

ORDER
REPRINTS
3050
DANIKIEWICZ AND SZMIGIELSKI
N-(cyclohexyloxymethyl)acetanilide. This can be rationalized by the follow-
ing reaction scheme:
The reason for such behaviour of cyclohexanol is not clear.
EXPERIMENTAL
1H and 13C NMR spectra were recorded on a Varian Gemini
(200 MHz) instrument in CDCl3 solution with tetramethylsilane as the inter-
nal standard. Mass spectra (EI, 70 eV) were obtained on AMD 604 (AMD
Intectra GmbH, Germany) instrument. Purity of the prepared samples was
checked by GC/MS analysis (HP 5890/5972A from Hewlett-Packard).
Anilides 2–4 utilised in the synthesis are commercially available (Aldrich).
Methoxymethylation of Anilides in PTC System.
General Procedure
To the suspension of anilide (2–4) (30 mmol), powdered KOH (or tert-
BuOK for4)(90 mmol)andtetrabutylammoniumhydrogensulfate(0.3 mmol)
in DMSO (or THF for 4) (50 mL) chloromethylmethyl ether (80 mmol) was
added dropwise. After 1 h agitation at room temperature the reaction mix-
ture was poured onto water and extracted with ethyl acetate (3 Â 15 mL).
The organic layer was dried over Na2SO4 and then the solvent was evapo-
rated under reduced pressure, yielding the crude product (5a–7a) to be

ORDER
REPRINTS
N-ALKOXYMETHYL DERIVATIVES
3051
purified by column chromatography on silica gel using hexane–ethyl acetate
mixture as an eluent.
N-(Methoxymethyl)acetanilide (5a). Yield: 85%. Oil. 1H NMR, d: 1.90
(s, 3H, COCH3); 3.42 (s, 3H, CH3); 5.04 (s, 2H, NCH2O); 7.18–7.48 (m, 5H,
Ph). 13C NMR, d: 22.7 (COCH3); 56.3 (OCH3); 78.6 (NCH2O); 128.0 (Ph);
.
129.5 (Ph); 142.1 (C-1 Ph); 171.5 (COCH3). MS m/z (%): 179 (Mþ , 48); 164
(50); 137 (15); 122 (19); 107 (11); 106 (100); 105 (58); 104 (23); 77 (35); 45
(44); 43 (32). HR MS calcd for C10H13NO2: 179.0946, found: 179.0952.
N-(Methoxymethyl)formanilide (6a). Yield: 90%. Oil. 1H NMR, d: 3.42
(s, 3H, OCH3); 5.13 (s, 2H, NCH2O); 7.23–7.50 (m, 5H, Ph); 8.56 (s, 1H,
CHO). 13C NMR, d: 57.2 (OCH3); 76.3 (NCH2O); 124.4 (Ph); 127.8 (Ph);
.
129.7 (Ph); 142.0 (C-1 Ph); 163.7 (CHO). MS m/z (%): 165 (Mþ , 29); 150
(24); 134 (10); 106 (46); 105 (30); 104 (29); 77 (42); 51 (13); 45 (100). HR MS
calcd for C9H11NO2: 165.0790, found: 165.0793.
N-(Methoxymethyl)benzanilide (7a). Yield: 73%. Oil. 1H NMR, d: 3.42
(s, 3H, OCH3); 5.19 (s, 2H, NCH2O); 7.02–7.34 (m, 10H, Ph). 13C NMR, d:
57.2 (OCH3); 80.7 (NCH2O); 127.4 (Ph); 127.8 (Ph); 128.3 (Ph); 129.3 (Ph);
129.6 (Ph); 130.6 (Ph); 135.6 (C-10 Ph); 143.5 (C-1 Ph); 171.9 (CHO). MS
.
m/z (%): 241 (Mþ , 31); 226 (30); 181 (10); 180 (12); 106 (16); 105 (100); 104
(17); 77 (71); 45 (30). HR MS calcd for C15H15NO2: 241.1102, found:
241.1099.
Transetherification of N-(Methoxymethyl)anilides.
General Procedure
Solution of N-(methoxymethyl)anilide (5a–7a) (20 mmol) and p-tolue-
nesulphonic acid (0.2 mmol) in the appropriate aliphatic alcohol (50 mL) was
heated during 1–4 h. (Only for compound 5i the mixture was allowed to stay
overnight at room temperature). The cooled reaction mixture was poured
into aqueous NaHCO3 solution and extracted with ethyl acetate
(3 Â 10 mL). The organic layer was dried over Na2SO4 and then the solvent
was removed under reduced pressure to produce oily product (5b–i, 6b, 7b) in
good yield which, when necessary, can be purified by column chromatogra-
phy on silica gel.
1
N-(Ethoxymethyl)acetanilide (5b). Oil. H NMR, d: 1.22 (t, 3H, J ¼
7 Hz, OCH2CH3); 1.88 (s, 3H, COCH3); 3.65 (q, 2H, J ¼ 7 Hz, OCH2CH3);
5.08 (s, 2H, NCH2O); 7.18–7.47 (5H, Ph). 13C NMR, d: 14.9 (CH3CH2O);
22.7 (COCH3); 64.0 (OCH2CH3); 76.9 (NCH2O); 127.9 (Ph); 129.5 (Ph); 142
.
(C-1 Ph); 171.3 (CO). MS m/z (%): 193 (Mþ , 3); 164 (73); 122 (40); 107 (13);
106 (100); 105 (57); 104 (31); 93 (51); 77 (52); 59 (25); 43 (35). HR MS calcd
for C11H15NO2: 193.1102, found: 193.1100.

ORDER
REPRINTS
3052
DANIKIEWICZ AND SZMIGIELSKI
N-(n-Propoxymethyl)acetanilide (5c). Oil. 1H NMR, d: 0.93 (t, 3H,
J ¼ 7.5 Hz, OCH2CH2CH3); 1.51–1.70 (m, 2H, OCH2CH2CH3); 1.89 (s,
3H, COCH3); 3.55 (t, 3H, J ¼ 6.8 Hz, OCH2CH2CH3); 5.09 (s, 2H, NCH2O);
7.20–7.50 (m, 5H, Ph). 13C NMR, d: 11.3 (OCH2CH2CH3); 23.5 (COCH3);
25.9(OCH2CH2CH3);71.2(OCH2CH2CH3);77.8(NCH2O);128.6(Ph);130.1
.
(Ph); 130.1 (Ph); 142.8 (C-1 Ph); 172.0 (CO). MS m/z (%): 207 (Mþ , 6); 164
(79); 149 (10); 122 (58); 107 (13); 106 (100); 105 (45); 104 (20); 94 (11); 93
(93); 77 (31); 43 (61). HR MS calcd for C12H17NO2: 207.1259, found:
207.1250.
1
N-(Isopropoxymethyl)acetanilide (5d). Oil. H NMR, d: 1.19 (d, 6H,
J ¼ 6.5 Hz, OCH(CH3)2); 1.88 (s, 3H, COCH3); 3.80–3.94 (m, 1H,
OCH(CH3)2); 5.10 (s, 2H, NCH2O); 7.20–7.44 (m, 5H, Ph). 13C NMR, d:
22.3 (OCH(CH3)2); 22.9 (COCH3); 69.5 (OCH(CH3)2); 75.1 (NCH2O); 128.0
(Ph); 128.2 (Ph); 129.5 (Ph); 142.4 (C-1 Ph); 171.4 (CO). MS m/z (%): 207
.
(Mþ , 10); 164 (55); 135 (16); 122 (24); 106 (45); 105 (14); 104 (12); 93 (100);
77 (19); 43 (24). HR MS calcd for C12H17NO2: 207.1259, found: 207.1257.
N-(n-Butoxymethyl)acetanilide (5e). Oil. 1H NMR, d: 0.91 (t, 3H,
J ¼ 7.3 Hz, OCH2CH2CH2CH3); 1.21–1.78 (m, 4H, OCH2CH2CH2CH3);
1.89 (s, 3H, COCH3); 3.58 (t, 2H, J ¼ 6.6 Hz, OCH2CH2CH2CH3); 5.08 (s, 2H,
NCH2O); 7.12–7.60 (m, 5H, Ph). 13C NMR, d: 13.9 (OCH2CH2CH2CH3);
19.3 (OCH2CH2CH2CH3); 22.9 (COCH3); 31.7 (OCH2CH2CH2CH3); 68.7
(OCH2CH2CH2CH3); 77.3 (NCH2O); 128.1 (Ph); 128.9 (Ph); 129.5 (Ph);
.
142.2 (C-1 Ph); 171.5 (CO). MS m/z (%): 221 (Mþ , 8); 164 (100); 149
(16); 148 (17); 135 (16); 122 (65); 106 (75); 105 (30); 93 (82); 77 (15); 57
(20); 43 (14). HR MS calcd for C13H19NO2: 221.1416, found: 221.1414.
1
N-(Iso-butoxymethyl)acetanilide (5f ). Oil. H NMR, d: 0.90 (d, 6H,
J ¼ 6.7 Hz, OCH2CH(CH3)2); 1.72–1.99 (m, 1H, OCH2CH(CH3)2); 1.89 (s,
3H, COCH3); 3.36 (d, 2H, J ¼ 6.6 Hz, OCH2CH(CH3)2); 5.09 (s, 2H,
NCH2O); 7.15–7.59 (m, 5H, Ph). 13C NMR, d: 19.4 (OCH2CH(CH3)2); 22.9
(COCH3); 28.5 (OCH2CH(CH3)2); 75.7 (OCH2CH(CH3)2); 77.4 (NCH2O);
128.1 (Ph); 128.8 (Ph); 129.5 (Ph); 142.2 (C-1 Ph); 171.5 (CO). MS m/z (%):
.
221 (Mþ , 17); 164 (58); 149 (12); 148 (17); 135 (15); 122 (63); 106 (74); 105
(32); 93 (100); 77 (15); 57 (20); 43 (14). HR MS calcd for C13H19NO2:
221.1416, found: 221.1411.
1
N-(Sec-butoxymethyl)acetanilide (5g). Oil. H NMR, d: 0.89 (t, 3H,
J ¼ 7.3 Hz), OCH(CH3)CH2CH3); 1.17 (d, 3H, J ¼ 6.1 Hz, OCH(CH3)CH2C-
CH3); 1.32–1.70 (m, 2H, OCH(CH3)CH2CH3); 1.88 (s, 3H, COCH3); 3.51–
3.78 (m, 1H, OCH(CH3)CH2CH3); 5.09 (s, 2H, NCH2O); 7.17–7.58 (m, 5H,
Ph). 13C NMR, d: 9.8 (OCH(CH3)CH2CH3); 19.4 (OCH(CH3)CH2CH3);
22.9 (COCH3); 24.6 (OCH(CH3)CH2CH3); 74.9 (OCH(CH3)CH2CH3);
75.5 (NCH2O); 128.1 (Ph); 129.0 (Ph); 129.5 (Ph); 141.1 (C-Ph); 170.9
.
(CO). MS m/z (%): 221 (Mþ , 1); 164 (45); 148 (12); 135 (23); 122 (20);

ORDER
REPRINTS
N-ALKOXYMETHYL DERIVATIVES
3053
106 (47); 93 (100); 77 (18); 57 (12); 43 (21). HR MS calcd for C13H19NO2:
221.1416, found: 221.1415.
1
N-(Tert-butoxymethyl)acetanilide (5h). Oil. H NMR, d: 1.20 (s, 9H,
OC(CH3)3); 1.85 (s, 3H, COCH3); 5.07 (s, 2H, NCH2O); 7.22–7.44 (m, 5H,
Ph). 13C NMR, d: 23.1 (COCH3); 27.9 (OC(CH3)3); 71.3 (OC(CH3)3); 73.4
(NCH2O); 127.9 (Ph); 128.5 (Ph); 129.2 (Ph); 142.5 (C-1 Ph); 170.6 (CO).
.
MS m/z (%): 221 (Mþ , 1); 164 (45); 148 (10); 135 (67); 122 (19); 106 (42);
105 (11); 104 (10); 93 (100); 77 (18); 57 (35); 43 (39); 41 (41). HR MS calcd
for C13H19NO2: 221.1416, found: 221.1420.
1
N-(n-Allyloxymethyl)acetanilide (5i). Oil. H NMR (CD3OD), d: 1.87
(s, 3H, COCH3); 4.08 (d, 2H, J ¼ 5.4 Hz, OCH2CH¼CH2); 5.06 (s, 2H,
NCH2O); 5.10–5.40 (m, 2H, OCH2CH¼CH2); 5.78–6.02 (m, 1H,
OCH2CH¼CH2); 7.15–7.59 (m, 5H, Ph). 13C NMR (CD3OD), d: 22.9
(COCH3); 70.5 (OCH2CH¼CH2); 77.9 (NCH2O); 117.3 (OCH2CH¼CH2);
129.3 (Ph); 129.4 (Ph); 130.7 (Ph); 135.4 (OCH2CH¼CH2); 142.3 (C-1 Ph);
.
172.0 (CO). MS m/z (%): 205 (Mþ , 1); 164 (51); 149 (17); 148 (39); 135 (23);
133 (24); 132 (36); 127 (15); 122 (49); 106 (100); 105 (29); 104 (23); 93 (47); 77
(20), 43 (47); 41 (80). HR MS calcd for C12H15NO2: 205.1103, found:
205.1102.
N-(Ethoxymethyl)formanilide (6b). Oil. 1H NMR, d: 1.22 (t, 3H,
J ¼ 7 Hz, OCH2CH3); 3.64 (q, 2H, J ¼ 7 Hz; OCH2CH3); 5.14 (s, 1H,
NCH2O); 6.82–7.60 (m, 5H, Ph); 8.56 (s, 1H, CHO). 13C NMR, d: 15.0
(OCH2CH3); 64.5 (OCH2CH3); 75.7 NCH2O); 125.4 (Ph); 127.1 (Ph);
.
129.2 (Ph); 144.2 (C-1 Ph); 163.2 (CHO). MS m/z (%): 179 (Mþ , 13); 150
(55); 135 (27); 122 (16); 106 (100); 105 (51); 104 (30); 93 (71); 77 (53); 66 (26);
65 (18); 59 (25); HR MS calcd for C10H13NO2: 179.0946, found: 179.0938.
1
N-(Ethoxymethyl)benzanilide (7b). Oil. H NMR, d: 1.24 (t, 3H, J ¼
7.6 Hz, OCH2CH3); 3.70 (q, 2H, J ¼ 6.9 Hz, OCH2CH3); 5.30 (s, 2H,
NCH2O); 7.05–7.40 (m, 10H, Ph). 13C NMR, d: 15.8 (OCH2CH3); 65.1
(OCH2CH3); 79.3 (NCH2O); 127.3 (Ph); 127.9 (Ph); 128.3 (Ph); 129.2
(Ph); 129.6 (Ph); 130.5 (Ph); 136.0 (C-10 Ph); 143.5 (C-1 Ph); 171.9 (CO).
.
MS m/z (%): 255 (Mþ , 6); 226 (27); 105 (100); 77 (36); 59 (6). HR MS calcd
for C16H17NO2: 255.1259, found: 255.1258.
REFERENCES
1. Vogl, Ch.; Aebi, R. German Patent (DBP) 2328 340, Ciba-Geigy (1973);
C.A. 1974, 80, 82440.
2. Vogl, Ch.; Aebi, R. Swiss Patent 576 945, Ciba-Geigy (1976); C.A. 1976,
85, 142866; Vogl, Ch.; Aebi, R. Swiss Patent 581 607, Ciba-Geigy
(1977); C.A. 1977, 86, 8586, 72242.

ORDER
REPRINTS
3054
DANIKIEWICZ AND SZMIGIELSKI
3. Vogl, Ch.; Aebi, R. US Patent 4 160 660 (1979); C.A. 1979, 91, 118677.
4. Kolpin, D.W.; Nations, B.K.; Goolsby, D.A.; Thurman, E.M.
Environ. Sci. Technol. 1996, 30, 1459.
5. Venkov, A.P.; Minkov, M.M.; Lukanov, L.K. Synth. Commun. 1989,
19, 2133.
6. Jacobsen, N.E.; Sanders, M.; Toia, R.F.; Casida, J.E. J. Agric. Food
Chem. 1991, 39, 1342.
7. Zupancic, B.G.; Sobcic, M. Synthesis 1982, 942.
8. Wedekind, E. German Patent (DRP) 135310 (1901); Chem. Zentralbl.
1902/II, 73, 1164.
9. Chiron, S.; Abian, J.; Ferres, M.; Sanches-Beaza, F.; Messeguer, A.;
Barcelo, D. Envirnon. Toxicol. Chem. 1995, 14, 1287.
10. Barluenga, J.; Bayon, M.A.; Campos, P.; Asensio, G.; Gonzalez-
Nunez, E.; Molina, Y. J. Chem. Soc. Perkin Trans. 1 1998, 1631.
11. Shono, T.; Matsumura, Y.; Inoue, K.; Ohmizu, H.; Kashimura, S.
J. Am. Chem. Soc. 1982, 104, 5753.
12. Villiger, V. Chem. Ber. 1909, 42, 3549.
13. Muzic, K.G.; Lapina, R.A. Zh. Obshch. Khim. 1953, 23, 1512.
Received in the Netherlands October 12, 2000

Request Permission or Order Reprints Instantly!
Interested in copying and sharing this article? In most cases, U.S. Copyright
Law requires that you get permission from the article’s rightsholder before
using copyrighted content.
All information and materials found in this article, including but not limited
to text, trademarks, patents, logos, graphics and images (the "Materials"), are
the copyrighted works and other forms of intellectual property of Marcel
Dekker, Inc., or its licensors. All rights not expressly granted are reserved.
Get permission to lawfully reproduce and distribute the Materials or order
reprints quickly and painlessly. Simply click on the "Request
Permission/Reprints Here" link below and follow the instructions. Visit the
U.S. Copyright Office for information on Fair Use limitations of U.S.
copyright law. Please refer to The Association of American Publishers’
(AAP) website for guidelines on Fair Use in the Classroom.
The Materials are for your personal use only and cannot be reformatted,
reposted, resold or distributed by electronic means or otherwise without
permission from Marcel Dekker, Inc. Marcel Dekker, Inc. grants you the
limited right to display the Materials only on your personal computer or
personal wireless device, and to copy and download single copies of such
Materials provided that any copyright, trademark or other notice appearing
on such Materials is also retained by, displayed, copied or downloaded as
part of the Materials and is not removed or obscured, and provided you do
not edit, modify, alter or enhance the Materials. Please refer to our Website
User Agreement for more details.
Order now!
Reprints of this article can also be ordered at
http://www.dekker.com/servlet/product/DOI/101081SCC100105679