MARCEL DEKKER, INC. • 270 MADISON AVENUE • NEW YORK, NY 10016
©
2003 Marcel Dekker, Inc. All rights reserved. This material may not be used or reproduced in any form without the express written permission of Marcel Dekker, Inc.
Yttria-Zirconia Based Lewis Acid Catalyst
4025
ꢀ
Cyclohexylcarbamic acid ethyl ester (3b). White solid. M.p.: 60 C. IR
ꢁ1
1
ꢀmax/cm (Neat): 3323, 2962, 1730, 1546, 1235. H NMR (200 MHz,
CDCl ) ꢁ: 1.11 (t, J ¼ 7.5, 3H), 1.15–2.25 (m, 10H), 3.15 (m, 1H), 3.45
3
(
bs, 1H), 4.10 (q, J ¼ 5.6, 2H).
ꢀ
Benzylcarbamic acid ethyl ester (3c). White solid. M.p.: 55 C. IR
ꢁ1
1
ꢀmax/cm (Nujol): 3450, 3018, 1711, 1516, 1216. H NMR (200 MHz,
CDCl ) ꢁ: 1.10 (t, J ¼ 7.5, 3H), 3.90 (q, J ¼ 5.6, 2H), 4.15 (d, J ¼ 5.3,
3
2
H), 7.05–7.50 (m, 5H), 8.50 (bs, 1H).
Phenylcarbamic acid methyl ester (3d). White solid. M.p.: 50 C. IR
ꢀ
ꢁ1
1
ꢀmax/cm (Nujol): 3291, 2950, 1730, 1543, 1216. H NMR (200 MHz,
CDCl ) ꢁ: 3.50 (s, 3H), 6.70 (bs, 1H), 7.10–7.40 (m, 5H).
3
ꢀ
Phenylcarbamic acid benzyl ester (3e). White solid. M.p.: 80 C. IR
ꢁ1
1
ꢀmax/cm (Nujol): 3431, 3019, 1731, 1525, 1214. H NMR (200 MHz,
CDCl ) ꢁ: 5.07 (s, 2H), 6.85–7.38 (m, 10H), 8.31 (bs, 1H).
3
ꢀ
p-Tolylcarbamic acid ethyl ester (3f). White solid. M.p.: 63 C. IR
ꢁ
1
1
(Nujol): 3318, 2981, 3019, 1706, 1529, 1229. H NMR
ꢀmax/cm
(
2
200 MHz, CDCl ) ꢁ: 1.25 (t, J ¼ 7.2, 3H), 2.60 (s, 3H), 4.20 (q, J ¼ 5.6,
3
H), 6.60 (bs, 1H), 7.10 (d, J ¼ 5.45, 2H), 7.25 (d, J ¼ 5.45, 2H).
ꢀ
p-Tolylcarbamic acid benzyl ester (3g). White solid. M.p.: 140 C. IR
ꢁ1
1
ꢀmax/cm (CHCl ): 3431, 3018, 1724, 1526, 1217. H NMR (200 MHz,
3
CDCl ) ꢁ: 2.32 (s, 3H), 5.21 (s, 2H), 6.68 (bs, 1H), 7.1–7.5 (m, 9H).
3
ꢀ
m-Tolylcarbamic acid methyl ester (3h). White solid. M.p.: 50 C. IR
ꢁ
1
1
ꢀmax/cm (CHCl ): 3430, 2922, 1713, 1457, 1226. H NMR (200 MHz,
3
CDCl ) ꢁ: 2.30 (s, 3H), 3.15 (s, 3H), 6.68 (bs, 1H), 7.10–7.80 (m, 4H).
3
(
4-Methoxyphenyl)carbamic acid ethyl ester (3i). White solid. M.p.:
ꢀ
ꢁ1
5–86 C. IR ꢀmax/cm (CHCl ): 3313, 2921, 1697, 1458, 1241. H NMR
3
1
8
(
2
200 MHz, CDCl ) ꢁ: 1.20 (t, J ¼ 7.25, 3H), 3.60 (s, 3H), 4.10 (q, J ¼ 5.9,
3
H), 6.70 (bs, 1H), 6.91 (d, J ¼ 6, 2H), 7.20 (d, J ¼ 6, 2H).
2-Hydroxyphenyl)carbamic acid ethyl ester (3j). White solid. M.p.:
(
0 C. IR ꢀmax/cm (CHCl ): 3224, 2921, 1700, 1456, 1231. H NMR
ꢀ
ꢁ1
1
8
3
(
(
200 MHz, CDCl ) ꢁ: 1.35 (t, J ¼ 7.16, 3H), 4.28 (q, J ¼ 5.9, 2H), 6.80
3
bs, 2H), 6.90–7.25 (m, 4H).
(
ꢀmax/cm (CHCl ): 3221, 2921, 1730, 1458, 1230. H NMR (200 MHz,
4-Nitrophenyl)carbamic acid ethyl ester (3k). Yellow solid. IR
1
ꢁ1
3
CDCl ) ꢁ: 1.34 (t, J ¼ 7.2, 3H), 4.28 (q, J ¼ 5.9, 2H), 7.06 (s, 1H), 7.80
3
(
d, J ¼ 8.9, 2H), 8.20 (d, J ¼ 8.9, 2H).
(
ꢀmax/cm
2-Acetoxyphenyl)carbamic acid ethyl ester (3l). Yellow oil. IR
1
ꢁ1
(CHCl ): 3446, 3018, 1726, 1705, 1582, 1220. H NMR
3
(
(
200 MHz, CDCl ) ꢁ: 1.34 (t, J ¼ 7.25, 3H), 2.64 (s, 3H), 4.28
3
q, J ¼ 5.9, 2H), 6.80 (bs, 1H), 7.10–7.88 (m, 4H).
ꢀ
Pyridin-2-yl-carbamic acid ethyl ester (3m). White solid. M.p.: 100 C.
(CHCl ): 3446, 3220, 3019, 1726, 1705, 1585, 1217.
3
ꢁ
1
IR ꢀmax/cm