982
S. Goumain et al.
PAPER
Table 2 1H and 13C NMR and MS Data of Compounds 3a
Prod-
uct
1H NMR (CDCl3/TMS)
d, J (Hz)
13 C{1H} NMR (CDCl3/TMS)
d, J (Hz)
MS (70 eV)
m/z (%)
(E)-3c
(Z)-3c
(E)-3db
(Z)-3db
(E)-3e
(Z)-3e
(E)-3fc
(Z)-3fc
1.3 (t, J = 7.1, 3H, CH3CH2O), 4.3 (q, J
= 7.1, 2H, CH3CH2O), 7.85 (s, 1H,
HC=CCl), 7.9 (d, J = 8.9, 2H, Ho-arom.),
13.1 (CH3CH2O), 62.1 (CH3CH2O),
122.6 (Cm-arom.), 125.1 (Ci-arom.), 130.1
(Co-arom.), 133.2 (HC=CCl), 138.1
(HC=CCl), 146.9 (CNO2), 161.5
(C=O)
257 (M+, 30), 255 (M+, 90), 220 (63),
210 (26), 192 (100), 164 (21), 147 (10),
136 (10), 101 (33), 89 (29), 75 (31), 51
(16), 38 (5)
8.2 (d, J = 8.9, 2H, Hm-arom.
)
1.1 (t, J = 7.1, 3H, CH3CH2O), 4.15 (q,
J = 7.1, 2H, CH3CH2O), 7.2 (s, 1H,
HC=CCl), 7.4 (d, J = 8.8, 2H, Ho-arom.),
12.7 (CH3CH2O), 61.6 (CH3CH2O),
122.5 (Cm-arom.), 125.6 (Ci-arom.), 128.3
(Co-arom.), 133.1 (HC=CCl), 139.4
(HC=CCl), 146.5 (CNO2), 161.5
(C=O)
257 (M+, 33), 255 (M+, 100), 220 (56),
192 (97), 164 (17), 147 (10), 136 (9),
101 (31), 89 (25), 75 (29), 51 (15), 36
(4)
8.1 (d, J = 8.8, 2H, Hm-arom.
)
1.35 (t, J = 7.1, 6H, CH3CH2O), 4.3 (m,
4H, CH3CH2O), 7 (d, J = 14.9, 1H, Hd),
7.2 (dd, J = 14.9, 8.4, 1H, Hg), 7.4 (m, 3
H, Harom), 7.5 (m, 2 H, Harom). , 7.6 (d, J
= 8.4, 1H, Hb)
12.7 (CH3CH2O), 60.7 (CH3CH2O),
121.1 (Ca), 121.5 (Cg), 126 (Co-arom),
127.3 (Cm-arom), 128 (Cp-arom), 134.4
(Ci-arom), 136.2 (Cb), 140.5 (Cd), 161.5
(C= O)
238 (M+, 17), 236( M+, 51), 209 (6),
207 (18), 193 (6), 191 (18), 155 (47),
129 (100), 128 (91), 127 (82), 115 (20),
91 (5), 77 (24), 51 (23), 50( 11), 34 (8)
1.35 (t, J = 7.1, 6H, CH3CH2O), 4.3 (m,
4H, CH3CH2O), 6.8 (d, J = 15.9, 1H,
Hd), 7 (d, J = 11.2, 1H, Hb), 7.4 (m, 3 H,
Harom), 7.5 (m, 2 H, Harom). , 7.9 (dd, J =
15.9, 11.2, 1H, Hg)
12.6 (CH3CH2O), 60.5 (CH3CH2O),
119.7 (Ca), 122.6 (Cg), 125.9 (Co-arom),
127.2 (Cm-arom), 127.7 (Cp-arom), 134.6
(Ci-arom), 139.6 (Cb), 140.6 (Cd), 161.2
(C=O)
238 (M+, 20), 236 (M+, 60), 209 (9),
207 (27), 193 (7), 191 (21), 155 (52),
129 (100), 128 (90), 127 (80), 115 (20),
91 (5), 77 (23), 51 (21), 50(9), 34 (8)
0.85 (m, 3H, CH3), 1.25 (m, 7H, CH2
and OCH2CH3), 1.4 (m, 2H, CH2), 2.3
(q, J = 7.5, 2H, CH2-CH=CCl), 4.2 (q, J
= 6.65, 2H, OCH2CH3), 7.0 (t, J = 7.25,
1H, CH2CH=CCl)
14.6 (CH3CH2O), 22.8 (CH3CH2), 27.8
(CH2), 29.8 (CH2), 31.9 (CH2), 62.5
(CH3CH2O), 123.6 (HC=ccl), 141.5
(HC=CCl), 161.6 (C=O)
206 (M+, 1), 204 (M+, 3), 180 (2), 178
(6), 169 (14), 159 (13), 141 (6), 135
(76), 122 (42), 107 (100), 95 (42), 83
(20), 70 (40), 55(59), 41 (83), 36 (1)
0.85 (m, 3H, CH3), 1.25 (m, 7H, CH2
and OCH2CH3), 1.4 (m, 2H, CH2), 2.5
(q, J = 7.5, 2H, CH2CH=CCl), 4.2 (q, J
= 6.65, 2H, OCH2CH3), 6.4 (t, J = 7.25,
1H, CH2CH=CCl)
14.3 (CH3CH2O), 22.8 (CH3CH2), 29.0
(CH2), 30.3 (CH2), 31.8 (CH2), 62.3
(CH3CH2O), 121.0 (HC=CCl), 141.1
(HC=CCl), 161.8 (C=O)
206 (M+, 17), 204 (M+, 51), 180 (33),
178 (11), 161 (27), 158 (15), 133 (100),
120 (34), 107 (76), 95 (32), 70 (67),
55(62), 41 (83), 36 (2)
1.3 (t, J = 7.1, 3H, CH3CH2O), 4.3 (q, J
= 7.1, 2H, CH3CH2O), 7.6 (d, J = 8.4,
2H, Ho-arom.), 7.8 (d, J = 8.1, 2H, Hm-
arom.), 7.85 (s, 1H, HC=CCl)
14.3 (CH3CH2O), 62.3 (CH3CH2O),
125.1 (Ci-arom.), 125.8 (q, J = 3.8, Cm-
arom.), 131 (Co-arom.), 131.4 (q, J = 36.1,
CCF3),135.6 (HC=CCl), 136.7
280 (M+, 26), 278 (M+, 78), 261 (6),
259 (18), 243 (41), 233 (29), 215 (100),
185 (35), 170 (55), 151 (40), 136 (19),
120 (18), 101 (14), 95 (9), 75 (34), 45
(17), 39 (4)
(HC=CCl), 163.3 (C=O), CdF3
1.1 (t, J = 7.1, 3H, CH3CH2O), 4.1 (q, J
= 7.1, 2H, CH3CH2O), 7.1 (s, 1H,
HC=CCl),7.3 (d, J = 8.2, 2H, Ho-arom.),
14 (CH3CH2O), 62.8 (CH3CH2O),
125.5 (Ci-arom.), 125.6 (q, J = 3.8, Cm-
arom.), 129.1 (Co-arom.), 132.3 (q, J = 36.1,
CCF3), 137.9 (HC=CCl), 163.3 (C=O),
CdF3
280 (M+, 32), 278 (M+, 96), 261 (6),
259 (18), 243 (50), 215 (100), 205 (34),
185 (33), 170 (54), 151 (36), 120 (16),
101 (12), 95 (8), 75 (29), 50 (12), 38 (4)
7.5 (d, J = 8.2, 2H, Hm-arom.
)
(E)-3g
(Z)-3g
1.4 (t, J = 7, 3H, CH3CH2O), 4.4 (q, J =
7, 2H, CH3CH2O), 7.2 (m, 2H, Harom.),
13.7 (CH3CH2O), 63.2 (CH3CH2O),
128.5 (Co-arom.), 129.2 (Cm-arom.), 129.5
280 (M+, 33), 278 (M+, 100), 251 (27),
249 (81), 235 (21), 233 (63), 205 (16),
185 (42), 169 (18), 151 (24), 129 (12),
101 (12), 99 (6), 75 (15), 51 (14), 39 (4)
7.4 (m, 3H, Harom.
)
(Cp-arom), 162.7 (C=O), CdF3, Cd
,
i-arom.
Cd(CF3), Cd(Cl)
0.9 (t, J = 7, 3H, CH3CH2O), 4 (q, J = 7,
2H, CH3CH2O), 7.2 (m, 2H, Harom.), 7.4
14.3 (CH3CH2O), 62.6 (CH3CH2O),
121.9 (q, J = 275.8, CF3), 128.3 (Co-
arom.), 129 (Cm-arom.), 129.4 (Cp-arom),
280 (M+, 33), 278 (M+, 100), 251 (24),
249 (72), 235 (13), 233 (39), 215 (14),
205 (12), 185 (44), 169 (21), 151 (27),
136 (13), 129 (8), 101 (17), 75 (21), 51
(22), 39 (7)
(m, 3H, Harom.
)
131.4 (q, J = 1.7, Ci-arom.), 133.8 (q, J =
32.4, C(CF3)), 162.6 (C=O), Cd(Cl)
a
The following products showed spectroscopic data in full agreement with previous reports refered in brackets: 3a (Ref. 4 and 11);
3b(Ref. 11).
b The subcript letters (a, b, ...) refer to the position relative to the ester group R1, namely : R1(Cl)Ca= CbHb-CgHg= CdHd-C6H5.
c 19F NMR (CDCl3), d = - 64.2 [(E)-3f] ; - 63.9 [(Z)-3f].
d Signal of very low intensity, not clearly detected.
Synthesis 1999, No. 6, 981–984 ISSN 0039-7881 © Thieme Stuttgart · New York