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5.3.1. (trans)-Methyl 1-n-butyl-3-phenyl aziridine car-
boxylate (4t). Colourless oil. Anal. calcd for C14H19NO2: C,
72.07; H, 8.21; N, 6. Found: C, 72.25; H, 8.36; N, 6.21.
EIMS m/z (rel int) 233 (Mþ, 5%), 232 (28), 190 (60), 176
(36), 174 (base), 118 (69), 117 (73), 116 (69), 91 (73), 90 (47),
89 (44). IR (film) 1727 cm21. 1H NMR (200 MHz, CDCl3) d
0.88 (t, J¼7.0 Hz, 3H), 1.10–1.60(m, 4H), 2.68 (d, J¼2.3 Hz,
1H), 2.77–3.04 (m, 2H), 3.10 (sl, 1H), 3.75 (s, 3H), 7.18–7.40
(m, 5H). 13C NMR (50 MHz, CDCl3) d 14, 20.3, 32.1, 44.2,
48.3, 51.3, 52.1, 126.2, 127.5, 128.3, 138.5, 169.2.
C18H18N2O5: C, 63.15; H, 5.3; N, 8.18. Found: C, 63.08; H,
1
5.22; N, 8.31. IR (film) 1727 cm21. H NMR (200 MHz,
CDCl3) d 2.70 (d, J¼6.3 Hz, 1H), 3.09 (d, J¼7.0 Hz, 1H),
3.48 (s, 3H), 3.56 (d, J¼12.5 Hz, 1H), 3.76 (s, 3H), 3.93 (d,
J¼13.3 Hz, 1H), 6.85 (d, J¼8.6 Hz, 2H), 7.30 (d, J¼8.6 Hz,
2H), 7.42 (t, J¼7.8 Hz, 1H), 7.72 (d, J¼7.8 Hz, 1H), 8.05
(dd, J1¼2.3 Hz, J2¼7.0 Hz, 1H), 8.23 (t, J¼2.3 Hz, 1H).
13C NMR (50 MHz, CDCl3) d 45.63, 46.34, 51.94, 55.18,
62.59, 113.9, 122.5, 123.0, 128.8, 129.0, 129.4, 134.1,
137.2, 147.9, 159.0, 168.0.
5.3.2. (cis)-Methyl 1-n-butyl-3-phenyl aziridine carboxyl-
ate (4c). White solid, mp 41–428C. Anal. calcd for
C14H19NO2: C, 72.07; H, 8.21; N, 6. Found: C, 72.12; H,
8.48; N, 6.08. EIMS m/z (rel int) 233 (Mþ, 6%), 232 (32),
190 (61), 176 (39), 174 (base), 118 (70), 117 (74), 116 (66),
91 (76), 90 (47), 89 (45). IR (CHCl3) 1746 cm21. 1H NMR
(200 MHz, CDCl3) d 0.89 (t, J¼7.8 Hz, 3H), 1.21–1.78 (m,
4H), 2.27 (ddd, J1¼6.3 Hz, J2¼8.6 Hz, J3¼11.7 Hz, 1H),
2.48 (d, J¼7.0 Hz, 1H), 2.77 (ddd, J1¼6.3 Hz, J2¼8.6 Hz,
J3¼11.7 Hz, 1H), 2.87 (d, J¼7.0 Hz, 1H), 3.44 (s, 3H),
7.15–7.40 (m, 5H). 13C NMR (50 MHz, CDCl3) d 14.0,
20.4, 31.4, 45.7, 48.0, 51.7, 60.5, 127.3, 127.6, 127.8, 135.3,
168.8.
5.3.7. (trans)-Methyl 1-[p-chlorobenzyl]-3-[m-nitrophe-
nyl]aziridine carboxylate (9t). White solid, mp 101–
1048C. Anal. calcd for C17H15N2O4Cl: C, 58.88; H, 4.36; N,
8.08. Found: C, 58.68; H, 4.41; N, 8.09. EIMS m/z (rel int)
346 (Mþ, 2%), 221 (base), 166 (36), 125 (59), 89 (38). IR
1
(CHCl3) 1728 cm21. H NMR (200 MHz, CDCl3) d 2.77
(d, J¼2.3 Hz, 1H), 3.39 (d, J¼1.6 Hz, 1H), 3.71 (s, 3H),
4.05 (d, J¼14.1 Hz, 1H), 4.21 (d, J¼14.1 Hz, 1H), 7.22–
7.32 (m, 4H), 7.46 (t, J¼7.8 Hz, 1H), 7.60 (d, J¼7.8 Hz,
1H), 8.10 (d, J¼9.4 Hz, 1H), 8.13 (s, 1H). 13C NMR
(50 MHz, CDCl3) d 44.60, 47.07, 52.41, 53.92, 121.2,
122.6, 128.5, 129.4 (2C), 132.4, 132.9, 136.9, 140.2, 148.3,
168.3.
5.3.3. (trans)-Methyl 1-benzyl-3-[m-nitrophenyl]aziri-
dine carboxylate (7t). Colorless oil. Anal. calcd for
C17H16N2O4: C, 65.37; H, 5.16; N, 8.97. Found: C, 65.53;
5.3.8. (cis)-Methyl 1-[p-chlorobenzyl]-3-[m-nitrophenyl]-
aziridine carboxylate (9c). Yellow solid, mp 98–1008C.
Anal. calcd for C17H15N2O4Cl: C, 58.88; H, 4.36; N, 8.08.
Found: C, 58.79; H, 4.43; N, 7.99. EIMS m/z (rel int) 346
(Mþ, 3%), 221 (base), 166 (36), 125 (58), 89 (40). IR
(CHCl3) 1746 cm21. 1H NMR (200 MHz, CDCl3) d 2.71 (d,
J¼7.0 Hz, 1H), 3.12 (d, J¼7.0 Hz, 1H), 3.49 (s, 3H), 3.64
(d, J¼13.3 Hz, 1H), 3.88 (d, J¼13.3 Hz, 1H), 7.23–7.49
(m, 5H), 7.74 (d, J¼7.8 Hz, 1H), 8.08 (d, J¼9.4 Hz, 1H),
8.24 (s, 1H). 13C NMR (50 MHz, CDCl3) d 45.98, 46.68,
52.03, 62.61, 122.7, 122.9, 128.7, 128.9, 129.2, 133.3,
134.0, 135.6, 136.9, 147.9, 167.7.
1
H, 5.19; N, 9.01. H NMR (200 MHz, CDCl3) d 2.73 (d,
J¼1.6 Hz, 1H), 3.35 (d, J¼1.6 Hz, 1H), 3.66 (s, 3H), 4.03
(d, J¼13.3 Hz, 1H), 4.18 (d, J¼13.3 Hz, 1H), 7.10–7.33
(m, 5H), 7.38 (t, J¼7.8 Hz, 1H), 7.54 (t, J¼7.8 Hz, 1H),
7.97–8.10 (m, 2H). 13C NMR (50 MHz, CDCl3) d 44.7,
47.0, 52.3, 54.7, 121.3, 122.5, 127.1, 128.0, 128.3, 129.3,
132.4, 138.4, 140.4, 148.3, 168.4.
5.3.4. (cis)-Methyl 1-benzyl-3-[m-nitrophenyl]aziridine
carboxylate (7c). White solid, mp 103–1058C. Anal. calcd
for C17H16N2O4: C, 65.37; H, 5.16; N, 8.97. Found: C,
65.40; H, 5.08; N, 8.84. EIMS m/z (rel int) 312 (Mþ, ,1%),
221 (base), 166 (33), 91 (63). 1H NMR (200 MHz, CDCl3) d
2.68 (d, J¼6.3 Hz, 1H), 3.08 (d, J¼7.0 Hz, 1H), 3.44 (s,
3H), 3.60 (d, J¼13.3 Hz, 1H), 3.93 (d, J¼13.3 Hz, 1H),
7.15–7.45 (m, 6H), 7.70 (d, J¼7.0 Hz, 1H), 8.01 (dd, J1¼
2.3 Hz, J2¼9.4 Hz, 1H), 8.20 (t, J¼2.3 Hz, 1H). 13C NMR
(50 MHz, CDCl3) d 45.9, 46.6, 52.0, 63.3, 122.6, 123.0,
127.6, 128.0, 128.5, 128.8, 134.1, 137.0, 137.1, 147.9, 167.9.
5.3.9. (cis)-Methyl 1-[20-hydroxyethyl]-3-[phenyl]aziri-
dine carboxylate (14c). Pale yellow oil. Anal. calcd for
C12H15NO3: C, 65.14; H, 6.83; N, 6.33. Found: C, 65.09; H,
6.89; N, 6.2. EIMS m/z (rel int) 220 (Mþ21, 7%), 162 (44),
168 (43), 56 (base). IR (CHCl3) 3430, 1731 cm21. 1H NMR
(200 MHz, CDCl3) d 2.61 (d, J¼7.0 Hz, 1H), 2.72 (dd, J1¼
5.5 Hz, J2¼10.2 Hz, 2H), 3.03 (d, J¼6.3 Hz, 1H), 3.50 (s,
3H), 3.82 (dd, J1¼5.5 Hz, J2¼10.2 Hz, 2H), 6.63 (sl, 1H),
7.15–7.55 (m, 5H). 13C NMR (50 MHz, CDCl3) d 42.4,
45.5, 47.6, 51.9, 61.6, 127.5, 128.0, 128.5, 132.5, 168.7.
5.3.5. (trans)-Methyl 1-[p-methoxybenzyl]-3-[m-nitro-
phenyl]aziridine carboxylate (8t). Yellow solid, mp
818C. Anal. calcd for C18H18N2O5: C, 63.15; H, 5.3; N,
8.18. Found: C, 63.02; H, 5.37; N, 8.08. IR (CHCl3)
5.3.10. (trans)-Bicyclo [4,1,0]1-oxa-2-oxo-4-phenyl-5-aza
heptane (15). Pale yellow oil. Anal. calcd for C11H11NO2:
C, 69.82; H, 5.86; N, 7.40. Found: C, 69.71; H, 5.98; N,
7.17. EIMS m/z (rel int) 189 (Mþ, 46%), 172 (46), 117 (93),
1
1728 cm21. H NMR (200 MHz, CDCl3) d 2.75 (d, J¼
1
1.6 Hz, 1H), 3.39 (d, J¼1.6 Hz, 1H), 3.72 (s, 3H), 3.76 (s,
3H), 4.01 (d, J¼14.1 Hz, 1H), 4.15 (d, J¼13.3 Hz, 1H), 6.83
(d, J¼7.8 Hz, 2H), 7.27 (d, J¼7.6 Hz, 2H), 7.44 (t,
J¼7.8 Hz, 1H), 7.59 (d, J¼7.8 Hz, 1H), 8.02–8.10 (m,
2H). 13C NMR (50 MHz, CDCl3) d 44.66, 47.03, 52.33,
54.08, 55.13, 113.7, 121.3, 122.5, 129.3, 129.4, 130.5,
132.4, 140.5, 148.3, 158.7, 168.5.
90 (base). IR (CHCl3) 1732 cm21. H NMR (200 MHz,
CDCl3) d 2.78 (d, J¼2.3 Hz, 1H), 3.20–3.50 (m, 2H), 3.67
(d, J¼2.3 Hz, 1H), 4.29 (dd, J1¼3.9 Hz, J2¼11.7 Hz, 1H),
4.48 (ddd, J1¼3.9 Hz, J2¼J3¼12 Hz, 1H), 7.18–7.40 (m,
5H). 13C NMR (50 MHz, CDCl3) d 39.4, 41.5, 42.7, 62.7,
126.3, 128.3, 128.7, 135.8, 166.6.
5.3.11. (cis)-Methyl 1-[20-N-acetylaminoethyl]-3-[phenyl]-
aziridine carboxylate (17c). White solid, mp product
instable upon heating. EIMS m/z (rel int) 263 (Mþþ1, 6%),
5.3.6. (cis)-Methyl 1-[p-methoxybenzyl]-3-[m-nitrophenyl]-
aziridine carboxylate (8c). Yellow oil. Anal. calcd for