1662
H. SLIMANI AND S. TOUIL
2b: Oil; 1H NMR: δ = 1.04 (t, 6H, 3JHH = 6.0, CH3-CH2-O;E); 1.14(t, 6H, 3JHH
=
2
2
6.0, CH3-CH2-O;Z); 2.12 (d, 2H, JPH = 25.0, CH2-P O;Z); 2.33(d, 2H, JPH = 15.0,
3
3
3
CH2-P O;Z); 3.88 (qp, 4H; JHH = JPH = 6.0, CH3-CH2-O;E); 4.04 (qp, 4H, JHH
3JPH = 6.0, CH3-CH2-O;Z); 6.50–7.80 (m, 10H, H arom); IR: νC N = 1642 cm−1; νP
=
=
O
1266 cm−1
;
13C NMR for arom-C: δ = 117.4, 119.5, 121.0, 123.7, 127.8, 128.0, 128.1,
128.3, 128.4, 128.7, 129.1, 129.3, 132.4, 133.0; ESI-MS: m/z = 349.428([M+NH4]+).
2c: Oil; 1H NMR: δ = 1.10 (t, 6H, 3JHH = 6.0, CH3-CH2-O;Z); 1.17 (t, 6H, 3JHH
=
6.0, CH3-CH2-O,E); 1.28 (d, 2H, 2JPH = 9.0, CH2-P = S, E); 1.60 (d, 2H, 2JPH = 9.0, CH2-
3
3
3
3
P S,Z); 3.92 (qp, 4H, JHH = JPH = 6.0, CH3-CH2-O,Z); 4.06 (qp, 4H, JHH = JPH
=
6.0, CH3-CH2-O,E); 6.21 (s, 2H, Ph-CH2,Z); 6.23 (s, 2H, Ph-CH2,E); 6.99–7.73 (m, 10H,
H arom); IR: νC = 1610 cm−1; νP = 1100 cm−1
;
13C NMR for arom-C: δ = 117.3,
N
S
125.5, 125.7, 125.9, 126.0, 126.9, 127.4, 127.6, 128.1, 128.7, 129.2, 130.9, 137.3, 137.5;
EI-MS: m/z = 361(M+, 15%); 345(30%); 332(16%); 270(60%); 91(100%); 77(28%).
2d: Oil; 1H NMR: δ = 1.19 (t, 3H, 3JHH = 7.0, CH3-CH2); 2.05 (d, 2H, 2JPH = 35.7,
CH2-P S); 3.04 (q, 2H, 3JHH = 7.0, CH3-CH2); 3.64 (s, 2H, Ph-CH2); 6.92–8.16 (m, 15H,
H arom). IR: νC = 1645 cm−1; νP = 1111 cm−1
;
13C NMR for arom-C: δ = 127.0,
N
S
127.2, 127.3, 127.6, 128.5, 128.7, 130.2, 130.3, 131.2, 132.8, 136.5, 137.6; EI-MS: m/z =
377(M+, 8%); 286(10%); 217(10%); 160(66%); 91(100%); 77(20%).
2e: Mp = 138◦C; 1H NMR: δ = 1.28 (t, 3H, 3JHH = 6.6, CH3-CH2); 2.22 (d, 2H, 2JPH
=
3
47.1, CH2-P O); 3.02 (q, 2H, JHH = 6.6, CH3-CH2); 3.66 (s, 2H, Ph-CH2); 7.14–7.54
(m, 15H, H arom). IR: νC N = 1646 cm−1; νP O = 1260 cm−1
;
13C NMR for arom-C: δ =
127.1, 127.3, 127.6, 127.7, 127.9, 128.1, 128.2, 128.9, 129.7, 131.2, 134.8, 136.6; EI-MS:
m/z = 361(M+, 33%); 270(13%); 201(53%); 160(86%); 91(100%); 77(29%).
2f: Oil; 1H NMR: δ = 1.08 (t, 6H, 3JHH = 6.0, CH3-CH2-O, Z); 1.19 (t, 6H, 3JHH
=
6.0, CH3-CH2-O, E); 1.25–3.05 (m, 7H, cyclic H and CH-P S); 3.79–4.15 (m, 6H, CH3-
CH2-O and Ph-CH2); 6.94–7.31 (m, 5H, H arom); IR: νC = 1616 cm−1; νP = 1096
N
S
cm−1
;
13C NMR for arom-C: δ = 125.1, 125.7, 127.0, 127.7, 128.2, 128.4, 132.9, 135.1;
EI-MS: m/z = 325(M+, 25%); 234(16%); 186(60%); 91(100%).
1
3
2g: Oil; H NMR: δ = 1.22 (t, 6H, JHH = 6.0; CH3-CH2-O); 1.39–3.20 (m, 7H,
cyclic H and CH-P O); 3.98–4.30 (m, 6H, CH3-CH2-O and Ph-CH2); 7.00–7.60 (m, 5H,
H arom); IR: νC = 1620 cm−1; νP = 1250 cm−1
;
13C NMR for arom-C: δ = 124.0,
N
O
125.2, 126.8, 131.9; EI-MS: m/z = 309(M+, 33%); 218(20%); 186(67%); 91(100%).
1
2h: Oil; H NMR: δ = 1.50–3.10 (m, 9H, cyclic H and CH-P S); 4.10 (s, 2H,
Ph-CH2); 6.90–8.20 (m, 15H, H arom). IR: νC = 1650 cm−1; νP = 1106 cm−1
;
13C
N
S
NMR for arom-C: δ = 127.5, 127.6, 128.0, 128.4, 128.5, 128.6, 128.7, 131.5, 131.6, 132.0,
133.1, 134.4; EI-MS: m/z = 403(M+, 16%); 312(20%); 217(29%); 186(75%); 91(100%);
77(25%).
1
3
3
2i: Oil; H NMR: δ = 1.07 (d, 6H, JHH = 6.0, CH3-CH-N); 1.22 (t, 6H, JHH
=
3
6.0, CH3-CH2-O); 1.38–2.25 (m, 9H, cyclic H and CH-P S); 3.36 (m, 1H, JHH = 6.0,
CH3-CH-N); 3.88–4.10 (m, 4H, CH3-CH2-O); IR: νC N = 1632 cm−1; νP S = 1097 cm−1
ESI-MS: m/z = 292.474([M+H]+).
;
1
3
2j: Oil; H NMR: δ = 1.18 (t, 6H, JHH = 7.2, CH3-CH2-O); 1.53–2.28 (m, 9H,
cyclic H and CH-P O); 3.80–4.05 (m, 6H, CH3-CH2-O and Ph-CH2); 7.04–7.30 (m, 5H,
H arom); IR: νC = 1631 cm−1; νP = 1254 cm−1
;
13C NMR for arom-C: δ = 126.0,
N
O
126.7, 127.8, 129.1; EI-MS: m/z = 323(M+, 36%); 232(15%); 186(62%); 91(100%).
2k: Mp = 176◦C; 1H NMR: δ = 1.50–2.50 (m, 9H, cyclic H and CH-P O); 5.52 (m,
2H, Ph-CH2); 7.00–8.30 (m, 15H, H arom); IR: νC N = 1664 cm−1; νP O = 1253 cm−1
;
13C
NMR for arom-C: δ = 127.5, 127.6, 127.9, 128.2, 128.4, 128.8, 129.0, 130.0, 130.8, 131.8,