PAPER
Highly Efficient Conversion of Alcohols to Isocyanides
439
Table 4 Spectral Data of Compound 2 7
Com-
pound
1H NMRa, b
, J (Hz)
13C NMRc, d
, J (Hz)
IR
(cm−1)
2
2.12 2.07 (m, 3 H), 2.06 2.00 (m, 6 H), 1.70
1.63 (m, 6 H)
151.65 (t, J = 5.0), 54.24 (t, J = 5.0), 43.58,
35.51, 28.74
(KBr) 2935, 2859, 2123
3a
3b
3.64 (t, 2 H, J = 6.6), 1.57 (quintet, 2 H, J = 6.9), 77.08, 63.03, 43.95, 32.77, 30.14, 29.54,
1.46 (m, 2 H), 1.38 1.24 (m, 12 H), 1.21 (s, 6 H) 29.54, 29.41, 29.20, 25.72, 24.33
(KBr) 3358 (br), 2966,
2923, 2970, 1184, 1070
3.66 (s, 3 H), 2.30 (t, 2 H, J = 7.4), 1.57 1.50 (m, 174.21, 71.04, 51.47, 44.02, 34017, 30.16,
(neat) 3348 (br), 2960,
2931, 2856, 1741, 1201,
1170
3 H), 1.49–1.42 (m, 2 H), 1.42 1.37 (m, 10 H),
29.47, 29.30, 29.25, 29.19, 25.02, 24.38
1.24 1.37 (m, 10 H), 1.20 (s, 6 H)
3c
3d
3e
3f
7.33 7.24 (m, 4 H), 7.15 (m, 1 H), 2.91 (t, 2 H,
J = 7.4), 1.64 (m, 2 H), 1.48 1.23 (m, 14 H), 1.20 33.68, 30.23, 29.63, 29.52, 29.32, 29.23,
(s, 6 H) 29.23, 28.90, 24.42
137.00, 128.81, 128.75, 125.59, 71.08, 44.06, (KBr) 3379 (br), 3078,
3057, 2968, 2927, 2854,
1853, 1481, 1153
7.83 (dd, 2 H, J = 5.4, 3.1), 7.70 (dd, 2 H, J = 5.4, 168.37, 133.76, 132.15, 123.10, 71.06, 44.06, (KBr) 3367 (br), 2969,
3.1), 3.67 (t, 2 H, J = 7.6), 1.67 (m, 2 H), 1.45 (m, 38.13, 30.16, 29.55, 29.44, 29.30, 29.20,
2 H), 1.37 1.22 (m, 12 H), 1.20 (s, 6 H) 28.64, 26.90, 24.37
2931, 2852, 1774, 1716,
1149
2.98 (t, 2 H, J = 7.7), 1.77 (quintet, 2 H, J = 7.7), 71.10, 43.89, 39.93, 29.89, 29.24, 29.24,
1.46 (m, 2 H), 1.40 (m, 2 H), 1.37 1.26 (m, 10 H), 29.02, 28.75, 27.53, 26.37, 24.14
1.20 (s, 6 H)
(KBr) 3384 (br), 3340
(br), 2937, 2980, 2850,
1633, 1139
5.44 (br s, 1 H), 3.23 (q, 2 H, J = 6.7), 1.97 (s, 3
H), 1.63 (br s, 1 H), 1.49 (m, 2 H), 1.46 (m, 2 H), 29.51, 29.43, 29.25, 29.25, 26.89, 24.31,
1.36 1.25 (m, 12 H), 1.21 (s, 6 H)
169.97, 71.03, 43.98, 39.70, 30.13, 29.62,
(KBr) 3330 (br), 3255
(br), 2971, 2929, 2848,
1656, 1560, 1186
23.39
4a
4b
4c
3.64 (t, 2 H, J = 6.6), 1.63 (br s, 1 H), 1.60 1.52
(m, 4 H), 1.48 1.41 (m, 2 H), 1.40 (t, 6 H, J = 1.8), 42.45, 32.76, 29.45, 29.45, 29.36, 29.36,
1.38 1.27 (m, 10 H) 28.97, 25.69, 24.10
152.57 (t, J = 4.3), 63.04, 57.43 (t, J = 5.0),
(neat) 3948 (br), 2983,
2929, 2854, 2130, 1070
3.66 (s, 3 H), 2.30 (t, 2 H, J = 7.4), 1.67 1.40 (m, 174.15, 152.79 (t, J = 4.2), 57.43 (t, J = 5.0),
6 H), 1.39 (t, 6 H, J = 1.8), 1.35 1.27 (m, 8 H)
(neat) 2983, 2935, 2856,
2130, 1739, 1201, 1170
51.47, 42.53, 34.15, 29.49, 29.31, 29.21,
29.15, 29.06, 29.98, 24.18
7.33 7.24 (m, 4 H), 7.15 (m, 1 H), 2.91 (t, 2 H,
152.76 (t, J = 4.2), 136.97, 128.82, 128.75,
(neat) 3078, 3057, 2981,
J = 7.4), 1.65 (m, 2 H), 1.58 1.39 (m, 4 H), 1.39 125.59, 57.45 (t, J = 5.0), 42.55, 33.67, 29.55, 2927, 2854, 2131, 1583,
(t, 6 H, J = 1.8), 1.33 1.26 (m, 10 H)
29.46, 29.45, 29.21, 29.19, 29.07, 28.86,
24.21
1481
4d
7.84 (dd, 2 H, J = 5.5, 3.1), 7.70 (dd, 2 H, J = 5.5, 168.48, 152.85 (t, J = 5.0), 133.85, 132.22,
(neat) 2981, 2933, 2856,
3.1), 3.68 (t, 2 H, J = 7.4), 1.67 (m, 2 H), 1.54 (m, 123.16, 57.41 (t, J = 5.0), 42.50, 38.06, 29.47, 2130, 1772, 1712
2 H), 1.39 (t, 6 H, J = 1.7), 1.49 1.23 (m, 12 H)
29.38, 29.36, 29.12, 28.99, 28.59, 26.82,
24.12
4e
4f
2.68 (t, 2 H, J = 6.9), 1.58 1.52 (m, 2 H), 1.48
1.40 (m, 4 H), 1.39 (t, 6 H, J = 1.8), 1.37 1.26 (m, 41.54, 33.15, 28.82, 28.81, 28.77, 28.72,
8 H)
151.96 (t, J = 5.0), 56.69 (t, J = 5.0), 41.79,
(neat) 3322 (br), 2981,
2927, 2854, 2130, 1579
28.31, 26.18, 23.45
5.49 (br s, 1 H), 3.23 (q, 2 H, J = 6.7), 1.97 (s,
3 H), 1.58 1.40 (m, 6 H), 1.39 (t, 6 H, J = 1.8 Hz), 42.51, 39.73, 29.66, 29.47, 29.41, 29.37,
1.35 1.23 (m, 10 H) 29.26, 29.06, 26.93, 24.15, 23.44
169.86, 152.66 (t, J = 5.0), 57.46 (t, J = 5.0),
(neat) 3295 (br), 2981,
29229, 2854, 2130, 1656,
1562
5a
6a
5b
1.75 1.69 (m, 4 H), 1.41 (m, 2 H), 1.31 (br s, 1 H), 71.03, 47.76, 40.93, 32.25, 27.67, 25.32,
1.21 (s, 3 H), 1.09 (m, 2 H), 1.00 (m, 1 H), 0.86 (s, 25.00
9 H)
(KBr) 3276 (br), 2969,
2933, 2861, 2840, 1139
1.68 (m, 2 H), 1.59 (m, 2 H), 1.38 1.26 (m, 4 H), 68.95, 47.68, 39.32, 32.40, 31.36, 27.62,
1.17 (br s, 1 H), 1.20 (s, 3 H), 0.92 (m, 1 H), 0.87 22.69
(s, 9 H)
(KBr) 3372 (br), 2960,
2930, 2865, 2840, 1126
3.89 (m, 1 H), 1.90 (m, 2 H), 1.75 (m, 2 H), 1.55
1.44 (m, 4 H), 1.28 (br s, 1 H), 1.27 (s, 3 H), 1.14
(br s, 1 H)
67.79, 67.77, 35.15, 30.46, 28.99
(KBr) 3313 (br), 3260
(br), 2956, 2923, 2863,
1135
Synthesis 2001, No. 3, 437–443 ISSN 0039-7881 © Thieme Stuttgart · New York