LETTER
Uchida, S. J. Chem. Soc., Chem. Commun. 1986, 1655.
(e) Uchida, S.; Yanada, K.; Yamaguchi, H.; Meguri, H.
Chem. Lett. 1986, 1069.
(18) Shi, Q. X.; Lu, R. W.; Jin, K.; Zhang, Z. X.; Zhao, D. F.
Protected N-Arylhydroxylamines
294.0589; found: 294.0589.
801
Methyl N-4-Iodophenyl-N-(methoxycarbonyloxy)
Carbamate
1H NMR (400 MHz, CDCl3): d = 7.63 (d, 2 H, J = 4.8 Hz),
Chem. Lett. 2006, 35, 226.
7.14 (d, 2 H, J = 4.8 Hz), 3.84 (s, 3 H), 3.77 (s, 3 H). 13
C
(19) Kin, B. H.; Cheong, J. W.; Han, R.; Jun, Y. M.; Baik, W.;
Lee, B. M. Synth. Commun. 2001, 31, 3577.
(20) Kin, B. H.; Jun, Y. M.; Suh, S. W.; Baik, W.; Lee, B. M.
J. Chem. Res., Synop. 1998, 46.
(21) Spectroscopic Data for New Compounds
Benzyl N-Phenyl-N-(benzoxycarbonyloxy) Carbamate
1H NMR (400 MHz, CDCl3): d = 7.47–7.45 (m, 2 H), 7.40–
7.26 (m, 13 H), 5.26 (s, 2 H), 5.22 (s, 2 H). 13C NMR (62.5
MHz, CDCl3): d = 154.2, 153.4, 139.4, 135.4, 134.1, 129.1,
129.0, 128.8, 128.7, 128.6, 128.5, 128.4, 128.0, 127.7,
124.0, 71.6, 68.6. HRMS: m/z calcd for [M + H]+
C22H19NO5Na: 400.1161; found: 400.1167.
NMR (62.5 MHz, CDCl3): d = 154.5, 153.5, 139.1, 138.1,
125.2, 92.3, 56.6, 54.2. HRMS: m/z calcd for [M + H]+
C10H11NO5127I: 351.9682; found: 351.9675.
Methyl N-4-Cyanophenyl-N-(methoxycarbonyloxy)
Carbamate
1H NMR (400 MHz, CDCl3): d = 7.63 (d, 2 H, J = 8.1 Hz),
7.58 (d, 2 H, J = 7.0 Hz), 3.94 (s, 3 H), 3.88 (s, 3 H). 13
C
NMR (62.5 MHz, CDCl3): d = 154.1, 152.5, 143.0, 133.0,
120.3, 118.3, 109.2, 57.0, 54.4. HRMS: m/z calcd for [M +
NH4]+ C11H14N3O5: 268.0928; found: 268.0931.
(22) Phenyl N-Phenyl-N-hydroxy Carbamate
1H NMR (400 MHz, CDCl3): d = 7.85 (br s, 1 H), 7.54 (d, 2
H, J = 7.8 Hz), 7.40–7.35 (m, 4 H), 7.26–7.22 (m, 2 H), 7.14
(d, 2 H, J = 7.8 Hz). 13C NMR (62.5 MHz, CDCl3):
d = 153.7, 150.7, 140.2, 129.5, 128.8, 126.5, 126.0, 122.5,
121.5. HRMS: m/z calcd for [M + H]+ C13H12NO3:
230.0812; found: 230.0812.
Benzyl N-4-Tolyl-N-(benzoxycarbonyloxy) Carbamate
1H NMR (400 MHz, CDCl3): d = 7.40–7.29 (m, 12 H), 7.18
(d, 2 H, J = 8.0 Hz), 5.27 (s, 2 H), 5.24 (s, 2 H), 2.25 (s, 3 H).
13C NMR (62.5 MHz, CDCl3): d = 154.7, 153.0, 140.7,
136.0, 135.5, 134.5, 129.7, 129.0, 128.8, 128.7, 128.6,
128.4, 122.0, 70.9, 67.2, 20.9. HRMS: m/z calcd for [M +
H]+ C23H22NO5: 392.1498; found: 392.1497.
Benzyl N-4-Cyano-N-(benzoxycarbonyloxy) Carbamate
1H NMR (400 MHz, CDCl3): d = 7.65–7.58 (m, 4 H), 7.39–
7.31 (m, 10 H), 5.28 (s, 2 H), 5.27 (s, 2 H). 13C NMR (62.5
MHz, CDCl3): d = 153.6, 151.9, 143.0, 134.7, 133.7, 133.0,
129.3, 128.8, 128.7, 128.6, 128.2, 120.1, 118.4, 109.1, 72.3,
69.2. HRMS: m/z calcd for [M + NH4]+ C23H22N3O5:
420.1559; found: 420.1570.
Phenyl N-4-Tolyl-N-hydroxy Carbamate
1H NMR (400 MHz, CDCl3): d = 7.88 (br s, 1 H), 7.41–7.33
(m, 4 H), 7.25–7.21 (m, 1 H), 7.19–7.11 (m, 4 H), 2.36 (s, 3
H). 13C NMR (62.5 MHz, CDCl3): d = 153.8, 150.8, 137.7,
136.7, 129.5, 129.4, 125.9, 123.0, 121.5, 21.0. HRMS: m/z
calcd for [M + NH4]+ C14H17N2O3: 261.1239; found:
261.1230.
Benzyl N-4-Tolyl-N-hydroxy Carbamate
1H NMR (400 MHz, CDCl3): d = 7.37–7.30 (m, 7 H), 7.15
(d, 2 H, J = 8.2 Hz), 5.21 (s, 2 H), 2.23 (s, 3 H). 13C NMR
(62.5 MHz, CDCl3): d = 155.6, 140.8, 138.4, 135.8, 129.2,
128.6, 128.1, 127.1, 122.7, 68.3, 21.0. HRMS: m/z calcd for
[M + H]+ C15H16NO3: 258.1125; found: 258.1126.
Benzyl N-4-Cyano-N-hydroxy Carbamate
Benzyl N-3-Trifluoromethylphenyl-N-(benzoxycarbonyl-
oxy) Carbamate
1H NMR (400 MHz, CDCl3): d = 7.74 (br s, 1 H), 7.66–7.64
(m, 1 H), 7.50–7.49 (m, 2 H), 7.39–7.30 (m, 10 H), 5.27 (s,
2 H), 5.26 (s, 2 H). 13C NMR (62.5 MHz, CDCl3): d = 153.9,
152.7, 140.0, 135.0, 133.9, 131.8 (q, CF3, J = 42 Hz), 129.6,
129.1, 128.8, 128.7, 128.6, 128.5, 128.1, 125.6, 123.6,
123.6, 119.5, 72.0, 69.0. HRMS: m/z calcd for [M + NH4]+
C23H22F3N2O5: 463.1481; found: 463.1472.
1H NMR (400 MHz, CDCl3): d = 7.70 (d, 2 H, J = 9.0 Hz),
7.58 (d, 2 H, J = 9.0 Hz), 7.43–7.33 (m, 5 H), 5.30 (s, 2 H).
13C NMR (62.5 MHz, CDCl3): d = 154.2, 144.7, 134.9,
132.7, 128.98, 128.4, 119.4, 118.8, 107.0 69.1. HRMS: m/z
calcd for [M + NH4]+ C15H16N3O3: 286.1192; found:
286.1194.
Methyl N-2-Tolyl-N-(methoxycarbonyloxy) Carbamate
1H NMR (400 MHz, CDCl3): d = 7.44 (d, 1 H, J = 7.8 Hz),
7.29–7.24 (m, 3 H), 3.88 (s, 3 H), 3.82 (s, 3 H), 2.37 (s, 3 H).
13C NMR (62.5 MHz, CDCl3): d = 154.8, 154.8, 137.8,
137.4, 131.1, 129.5, 128.5, 126.7, 56.2, 54.0, 17.16. HRMS:
m/z calcd for [M + H]+ C11H14NO5: 240.0872; found:
240.0867.
Methyl N-3-Tolyl-N-(methoxycarbonyloxy) Carbamate
1H NMR (500 MHz, CDCl3): d = 7.31–7.28 (m, 3 H), 7.15
(d, 1 H, J = 7.0 Hz), 3.94 (s, 3 H), 3.87 (s, 3 H), 2.39 (s, 3 H).
13C NMR (125 MHz, CDCl3): d = 154.7, 154.1, 139.2,
139.1, 128.9, 128.8, 125.1, 121.5, 56.4, 54.0, 21.5. HRMS:
m/z calcd for [M + H]+ C11H14NO5: 240.0872; found:
240.0863.
Benzyl N-3-Trifluoromethylphenyl-N-hydroxy
Carbamate
1H NMR (400 MHz, CDCl3): d = 7.68 (br s, 1 H), 7.56–7.55
(m, 1 H), 7.31–7.29 (m, 2 H), 7.21–7.13 (m, 5 H), 5.10 (s, 2
H). 13C NMR (62.5 MHz, CDCl3): d = 155.0, 141.4, 135.0,
131.0 (q, J = 32 Hz, CF3), 129.1, 128.7, 128.7, 128.2, 127.8,
127.1, 124.2, 118.1, 69.0. HRMS: m/z calcd for [M + NH4]+
C15H16FN2O3: 329.1108; found: 329.1110.
Methyl N-2-Tolyl-N-hydroxy Carbamate
1H NMR (400 MHz, CDCl3): d = 9.0 (br s, 1 H), 7.36–7.33
(m, 1 H), 7.28–7.22 (m, 3 H), 3.75 (s, 3 H), 2.34 (s, 3 H). 13
C
NMR (62.5 MHz, CDCl3): d = 157.5, 139.5, 136.2, 130.9,
128.9, 127.5, 126.6, 53.8, 17.6. HRMS: m/z calcd for [M +
Na]+ C9H11NO3Na: 204.0631; found: 204.0634.
Methyl N-4-Tolyl-N-(methoxycarbonyloxy) Carbamate
1H NMR (400 MHz, CDCl3): d = 7.34 (d, 2 H, J = 8.1 Hz),
7.19 (d, 2 H, J = 8.1 Hz), 3.90 (s, 3 H), 3.83 (s, 3 H), 2.36 (s,
3 H). 13C NMR (62.5 MHz, CDCl3): d = 154.8, 154.3, 138.4,
136.8, 129.7, 125.1, 56.3, 53.9, 21.1. HRMS: m/z calcd for
[M + H]+ C11H11NO5: 240.0866; found: 240.0868.
Methyl N-3-Trifluoromethylphenyl-N-(methoxycar-
bonyloxy) Carbamate
Methyl N-3-Tolyl-N-hydroxy Carbamate
1H NMR (400 MHz, CDCl3): d = 8.2 (br s, 1 H), 7.33–7.28
(m, 3 H), 7.06 (d, 2 H, J = 6.6 Hz), 3.84 (s, 3 H), 2.40 (s, 3
H). 13C NMR (62.5 MHz, CDCl3): d = 156.4, 140.9, 138.5,
128.4, 126.9, 123.1, 119.7, 53.7, 21.5. HRMS: m/z calcd for
[M]+ C9H11NO3: 181.0739; found: 181.0735.
1H NMR (400 MHz, CDCl3): d = 7.75 (s, 1 H), 7.68–7.66
Methyl N-4-Tolyl-N-hydroxy Carbamate
(m, 1 H), 7.54–7.52 (m, 2 H), 3.96 (s, 3 H), 3.89 (s, 3 H). 13
C
1H NMR (400 MHz, CDCl3): d = 2.34 (s, 3 H), 3.77 (s, 3 H),
7.15 (d, 2 H, J = 8.2 Hz), 7.33 (d, 2 H, J = 8.2 Hz), 8.55 (br
s, 1 H). 13C NMR (62.5 MHz, CDCl3): d = 156.4, 138.4,
136.2, 129.2, 122.8, 53.7, 21.0. HRMS: m/z calcd for [M +
NMR (62.5 MHz, CDCl3): d = 154.4, 153.4, 139.9, 131.4 (q,
CF3, J = 32 Hz), 129.5, 125.9, 123.8, 121.4, 119.6, 56.7,
54.2. HRMS: m/z calcd for [M + H]+ C11H11NO5F3:
Synlett 2009, No. 5, 798–802 © Thieme Stuttgart · New York