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S. Sengmany et al.
PAPER
Table 2 Spectral Data for Cyclopropanes 1,6–15a
Product
No. IR (film)
(cm–1)
1H NMR (200 MHz, CDCl3) ,
J (Hz)
13C NMR
(50.32 MHz, CDCl3)
MS m/z (%)
1
3010, 2970, 7.4–7.1 (m, 10 H), 3.6 (s, 3 H), 3.3 (s, 172.0, 171.9, 141.2,
1760–1730, 3 H), 3.3 (d, 1 H, J = 17.5), 2.45 (d, 1 141.0, 128.9, 128.6,
324 (1), 293 (10), 292 (21), 265 (10), 264
(48), 261 (31), 260 (92), 250 (10), 233 (24),
232 (66), 231 (16), 206 (13), 205 (77), 204
(52), 203 (30), 202 (17), 192 (10), 191 (36),
190 (12), 189 (13), 178 (14), 168 (14), 167
(100), 166 (10), 165 (34), 152 (11)
1600, 1590, H, J = 5.9), 1.7 (d, 1 H, J = 17.5),
1490, 1450 1.65 (d, 1 H, J = 5.9)
128.5, 128.2, 126.9,
126.5, 51.5, 43.8,
37.6, 32.2, 22.9
6
7
3030, 2990, 7.8–7.5 (m, 10 H), 2.45 (dd, 1 H, J = 142.3, 139.1, 129.5,
2220, 1600, 9, 5.7), 2.25 (dd, 1H, J = 5.7, 5.2), 2.0 128.8, 127.8, 127.4,
218 (70), 203 (9), 192 (100), 178 (11), 165
(25), 141 (63), 115 (7)
1500, 1450 (dd, 1 H, J = 9, 5.2)
119.5, 38.2, 21.0,
12.2
3020, 1750– (R*,S*): 3.7 (s, 3 H), 3.65 (s, 3 H),
(R*,S*):168.4, 166.7, (R*,S*):194 (1), 192 (3), 163 (26), 161 (84),
1730
2.4 (dd, 1 H, J = 11, 8.3), 2.1 (dd, 1 53.3, 52.4, 42.8, 31.6, 157 (100), 156 (69), 135 (28), 134 (51), 133
H, J = 11, 7), 1.6 (dd, 1 H, J = 8.3, 7) 22.3
(77), 132 (76), 131 (25), 125 (20), 117 (11),
(R*,R*): 3.65 (s, 3 H), 3.6 (s, 3 H),
(R*,R*):168.8, 167.3, 105 (37), 98 (15)
2.5 (m, 1 H), 1.8 (m, 2 H)
53.7, 52.5, 42.2, 30.6, (R*,R*): 194 (1), 192 (3), 163 (10), 161
22.9
(34), 157 (100), 156 (94), 135 (22), 134
(43), 133 (39), 132 (85), 131 (11), 125 (19),
117 (13), 105 (16), 97 (16)
8
3030, 2990, (R*,R*): 7.6–7.3 (m, 5 H), 3.8 (s, 3
1740, 1600, H), 2.3 (dd, 1 H, J = 9.1, 7.8), 2.05
(R*,R*): 168.8,
141.1, 129.1, 128.4,
(R*,R*): 212 (3), 210 (11), 178 (13), 175
(46), 151 (20), 150 (19), 116 (46), 115 (100)
1500, 1450 (dd, 1 H, J = 7.8, 6.1), 1.75 (dd, 1 H, 126, 51.8, 47.5, 29.5, (R*,S*): 212 (3), 210 (14), 178 (13), 175
J = 9.1, 6.1)
21.3
(45), 151 (17), 115 (100)
(R*,S*): 7.4–7.2 (m, 5 H), 3.4 (s, 3
(R*,S*):169.2, 137.6,
H), 2.6 (dd, 1 H, J = 9.7, 7.3), 2.1 (dd, 129, 128.7, 128.5, 52,
1 H, J = 7.3, 6), 1.8 (dd, 1 H, J = 9.7, 48.6, 31.2, 21.4
6)
9
3030, 3010, 7.8-7.4 (m, 10 H), 3.8 (s, 3 H), 2.9
171.0, 144.8, 140.3,
2960, 1730, (dd, 1 H, J = 7.9, 6.1), 2.5 (dd, 1 H, J 129.7, 128.5, 128.4,
1600, 1580, = 6.1, 4.9), 1.9 (dd, 1 H, J = 7.9, 4.8) 127.6, 127.1, 126.6,
252 (1), 221 (5), 192 (100), 178 (20), 165
(15), 115 (20)
1500, 1450
51.6, 40.0, 28.9, 20.2
10 3030, 3010, cis: 7.2-6.8 (m, 5 H), 3.3 (s, 3 H), 2.5 cis: 171.0, 136.4,
cis: 176 (26), 144 (58), 121 (18), 117 (100),
2970, 1735, (m, 1 H), 2.0 (dt, 1 H, J = 9.2, 6.5),
128.2, 127.8, 127.3,
116 (71), 115 (79), 91 (18), 77 (4), 65 (4), 51
1600, 1500, 1.7–1.1 (m, 2 H)
51.1, 25.5, 21.5, 11.2 (4)
trans: 176 (30), 144 (68), 121 (18), 117
(100), 116 (78), 115 (89), 91 (21), 77 (5), 63
51.6, 26.1, 23.8, 16.9 (6), 51 (4)
1450
trans: 7.2–6.8 (m, 5 H), 3.6 (s, 3 H), trans: 173.5, 139.8,
2.5 (m, 1 H), 1.8 (dt, 1 H, J = 9.7, 5), 128.4, 126.4, 126.0,
1.55–1.1 (m, 2 H)
11 1760–1720 (R*,S*): 3.76 (s, 3 H), 3.70 (s, 3 H), (R*,S*) : 170.6,
3.64 (s, 3 H), 3.10 (d, 1 H, J = 17.4), 169.4, 166.5, 53.2,
(R*,S*): 266 (1), 264 (9), 235 (20), 234 (18),
233 (59), 232 (50), 228 (49), 205 (57), 202
2.7 (d, 1 H, J = 17.4), 2.36 (d, 1 H, J 53.1, 52.6, 48.5, 35.8, (39), 201 (62), 200 (98), 198 (18), 197 (50),
= 7.2), 1.41 (d, 1 H, J = 7.2)
(R*,R*): 3.76 (s, 3 H), 3.70 (s, 3 H), (R*,R*): 170.4,
3.61 (s, 3 H), 3.00 (d, 1 H, J = 17), 167.7, 167.3, 53.4,
32.8, 26.2
191 (22), 178 (12), 175 (28), 174 (20), 173
(87), 172 (20), 171 (25), 170 (31), 169
(100), 165 (17), 145 (19)
2.55 (d, 1 H, J = 17), 2.20 (d, 1 H, J 52.4, 51.6, 44.7, 36.4, (R*,R*): 266 (12), 264 (20), 235 (14), 234
= 6.8), 1.90 (d, 1 H, J = 6.8)
33.8, 25.5
(21), 233 (42), 232 (43), 228 (29), 205 (29),
202 (31), 201 (33), 200 (100), 198 (16), 197
(42), 177 (16), 175 (29), 174 (38), 173 (68),
172 (21), 169 (85), 147 (21), 145 (16)
12 3030, 2970, (R*,S*): 7.3–7.0 (m, 5 H), 3.6 (s, 3
1760–1730, H), 3.15 (s, 3 H), 2.75 (d, 1 H, J =
Mixture of the two di- (R*,S*): 248 (26), 217 (30), 185 (12), 184
astereoisomers (29), 130 (15), 129 (100), 128 (47), 127
1600, 1590, 17.3), 2.45 (d, 1 H, J = 17.3), 2.4 (dd, (R*,S*) and (R*,R*): (12), 115 (11), 59 (12), 51 (12)
1490, 1450 1 H, J = 8.7, 6.5), 1.9 (dd, 1 H, J =
6.5, 5.4), 1.1 (dd, 1 H, J = 8.7, 5.4)
174, 171.9, 135.7,
129, 128.1, 126.9, 52, (19), 184 (37), 130 (15), 129 (100), 128
51.3, 39.8, 30.6, 26.7, (61), 121 (13), 115 (22), 63 (10), 59 (12), 51
(R*,R*): 248 (54), 217 (42), 216 (17), 185
(R*,R*): 7.3–7.1 (m, 5 H), 3.7 (s, 3
H), 3.5 (s, 3 H), 2.9 (dd, 1 H, J = 9.3, 18.3
6.7), 2.45 (d, 1 H, J = 17.3), 1.95 (d,
1 H, J = 17.3), 1.8 (dd, 1 H, J = 9.3,
5.3), 1.4 (dd, 1 H, J = 6.7, 5.3)
(13)
Synthesis 2002, No. 4, 533–537 ISSN 0039-7881 © Thieme Stuttgart · New York