J
S. M. Masjed et al.
1
1
7
918, 1739, 1608, 1507, 1452, 1379, 1245, 1177, 1113,
047, 957, 819, 703, 547, 438 cm . dH (CDCl , 400 MHz)
3
.53 (d, J 8.2, 2H, Ar), 7.27 (d, J 8.2, 2H, Ar), 2.42 (s, 3H, CH3).
100 MHz) 133.2, 132.8, 132.5, 132.3, 128.6, 128.5, 127.5,
þ
53]
ꢁ1
125.0, 124.8, 117.7, 110.1. m/z (ESI) 153 (100 %, M ).
[
Hexanenitrile (Table 4, Entry 20). Oil (Lit.
oil). dH
(CDCl , 300 MHz) 2.34 (t, J 12.0, 2H, CH ), 1.72–1.62
d (CDCl , 100 MHz) 143.6, 131.9, 129.7, 119.1, 109.2, 21.7.
C
3
3
2
þ
m/z (ESI) 117 (19 %, M ).
-Methylbenzonitrile (Table 4, Entry 8). Oil (Lit.
(m, 2H, CH ), 1.49–1.32 (m, 4H, CH ), 0.93 (t, J 12.0, 3H,
2 2
[47]
2
oil).
nmax (neat)/cm 3064, 3038, 2962, 2925, 2865, 2227 (CN),
CH ). d (CDCl , 75 MHz) 119.7, 30.6, 24.9, 21.7, 16.9, 13.5.
3 C 3
ꢁ
1
[54]
Octanenitrile (Table 4, Entry 21). Oil (Lit.
ꢁ
oil). nmax
(neat)/cm 2962, 2930, 2859, 2246 (CN), 1462, 1427, 1377,
1
1
6
608, 1508, 1450, 1412, 1382, 1177, 1120, 1041, 955, 817, 710,
þ
þ
69, 546, 439. m/z (ESI) 117 (10 %, M ).
4
1119, 723. m/z (ESI) 125 (2 %, M ).
3-Methylbutanenitrile (Table 4, Entry 22). Oil (Lit.
nmax (neat)/cm 3648, 2966, 2933, 2876, 2246, 1467, 1425,
1391, 1342, 1282, 1171, 1114, 935, 891, 820. m/z (ESI) 83
[
20]
[55]
-Isopropylbenzonitrile (Table 4, Entry 9). Oil (Lit.
ꢁ
oil).
oil).
1
ꢁ1
nmax (neat)/cm 3078, 2965, 2929, 2872, 2228 (CN), 1737,
1
8
684, 1606, 1503, 1460, 1366, 1244, 1197, 1100, 1053, 1018,
þ
þ
38, 761, 695, 566. m/z (ESI) 145 (17 %, M ).
(3 %, M ).
4
28C (Lit.
-(Dimethylamino)benzonitrile (Table 4, Entry 10). Mp 70–
[
48]
ꢁ1
7
2
9
72–758C). nmax (KBr)/cm 2917, 2864, 2814,
207 (CN), 1606, 1524, 1446, 1368, 1227, 1171, 1125, 1066,
Supplementary Material
þ
38, 817, 645, 544. m/z (ESI) 146 (95 %, M ).
4
Details of analysis of nitrile derivatives are available on the
Journal’s website.
-Chlorobenzonitrile (Table 4, Entry 11). Mp 89–918C
[
43]
ꢁ1
3086, 3043, 2974, 2218
CN), 1909, 1783, 1662, 1584, 1481, 1393, 1267, 1180, 1083,
(
(
Lit.
928C). nmax (KBr)/cm
Acknowledgements
1
2
1
009, 826, 703, 580, 539. d (CDCl , 400 MHz) 7.61 (d, J 8.6,
H 3
H, Ar), 7.47 (d, J 8.6, 2H, Ar). d (CDCl , 100 MHz) 139.5,
C
The authors gratefully acknowledge the partial support of this study by
Ferdowsi University of Mashhad Research Council (grant no. p/3/38854).
3
þ
33.3, 129.6, 117.9, 110.7. m/z (ESI) 137 (85 %, M ).
,6-Dichlorobenzonitrile (Table 4, Entry 12). Mp 140–1438C
2
[
49]
ꢁ1
References
(
Lit.
142–1458C). nmax (KBr)/cm 3145, 3090, 2230 (CN),
748, 1706, 1571, 1509, 1430, 1228, 1196, 1102, 782, 714, 547.
[
1] (a) R. C. Larock, Comprehensive Organic Transformations 1989
1
m/z (ESI) 172 (92 %, M ).
þ
(VCH: New York, NY).
(
b) C. Grundmann, in Houben-Weyl: Methodender Organischen
4
-Bromobenzonitrile (Table 4, Entry 13). Mp 112–1138C
Chemie (Ed. J. Falbe) 1985, pp. 1313–1527 (Georg Thieme: Stuttgart).
[
46]
ꢁ1
(
Lit. 113–1158C). nmax (KBr)/cm 3106, 3060, 2991, 2933,
[
2
1
857, 2227 (CN), 1603, 1527, 1437, 1346, 1288, 1190, 1103,
þ
010, 858, 749, 679, 540. m/z (ESI) 182 (100 %, M ).
4
(
b) P. C. Ducept, S. P. Marsden, Synlett 2000, 692.
-Nitrobenzonitrile (Table 4, Entry 14). Mp 146–1488C
[
50]
ꢁ1
(
Lit.
1498C). nmax (KBr)/cm 3059, 2963, 2926, 2855,
224 (CN), 1733, 1687, 1584, 1503, 1380, 1343, 1240, 1157,
2
1
8
1
(b) M. Chihiro, H. Nagamoto, I. Takemura, K. Kitano, H. Komatsu,
062, 1013, 961, 806, 770, 693, 587, 457. d (CDCl , 400 MHz)
H
3
.37 (d, J 8.8, 2H, Ar), 7.91 (d, J 8.8, 2H, Ar). dC (CDCl3,
00 MHz) 150.0, 133.4, 124.2, 118.3, 116.8. m/z (ESI) 148
[
þ
(
45 %, M ).
Terephthalonitrile (Table 4, Entry 15). Mp 218–2208C
Lit.
2
1
(
b) T. R. Bailey, G. D. Diana, P. J. Kowalczyk, V. Akullian, M. A.
[
17]
ꢁ1
(
219–2208C). nmax (KBr)/cm 3096, 3050, 2962,
924, 2854, 2230 (CN), 1941, 1809, 1692, 1500, 1402, 1276,
(
c) P. K. Kadaba, Synthesis 1973, 71.
198, 1025, 844, 641, 561. d (CDCl , 400 MHz) 7.81 (s, 4H,
3
[5] G. K. Jnaneshwara, V. H. Deshpande, M. Lalithambika,
H
Ar). d (CDCl , 100 MHz) 132.8, 117.0, 116.7. m/z (ESI) 128
C
3
þ
(
(
5 %, M ).
-Cyanopyridine (Table 4, Entry 16). Oil (Lit.
[
41]
[
2
oil). nmax
neat)/cm 2917, 2864, 2814, 2207 (CN), 1606, 1524, 1446,
368, 1227, 1171, 1125, 1066, 938, 817, 645, 544. d (400 MHz,
ꢁ
1
[
7] M. E. Fabiani, Drug News Perspect. 1999, 12, 207.
9] (a) T. Sandmeyer, Ber. Dtsch. Chem. Ges. 1885, 18, 1946.
1
H
[
CDCl ) 7.35 (s, 1H, Py), 7.74 (s, 1H, Py), 7.844 (d, J 6.4,
3
H, Py), 8.51 (s, 1H, Py). m/z (ESI) 104 (12 %, M ).
þ
1
[
[
51]
3
8–518C). nmax (KBr)/cm 3141, 3083, 3026, 2990 (CN), 2239,
-Cyanopyridine (Table 4, Entry 17). Mp 46–508C (Lit.
(
ꢁ1
4
1
1
973, 1718, 1591, 1543, 1493, 1414, 1331, 1236, 1206, 1111,
þ
081, 987, 827, 775, 559. m/z (ESI) 104 (12 %, M ).
Thiophen-2-carbonitrile (Table 4, Entry 18). Oil (Lit. oil).
[
52]
ꢁ
1
1
nmax (neat)/cm 3109, 3098, 2221 (CN), 1413, 1349, 1232,
1
157, 1077, 1040, 856, 719, 567, 524, 486. m/z (ESI) 109
þ
(
30 %, M ).
1
[
16]
-Naphthonitrile (Table 4, Entry 19). Mp 32–348C (Lit.
ꢁ1
3
1
5
8
7
48C). nmax (neat)/cm 3058, 2926, 2847, 2222 (CN), 1625,
586, 1508, 1375, 1342, 1242, 1162, 1047, 863, 803, 772, 689,
72, 453. d (CDCl , 400 MHz) 8.21 (d, J 8.0, 1H, Ar), 8.05 (d, J
H
.0, 1H, Ar), 7.92–7.88 (m, 2H, Ar), 7.69–7.66 (m, 1H, Ar),
.62–7.7.58 (m, 1H, Ar), 7.52–7.48 (m, 1H, Ar). d (CDCl ,
[
12] (a) S. H. Khezri, N. Azimi, M. Mohammed-Vali, B. Eftekhari-Sis,
M. M. Hashemi, M. H. Baniasadi, F. Teimouric, ARKIVOC 2007,
15, 162.
3
C
3