Noor-ul H. Khan et al. / Journal of Organometallic Chemistry 692 (2007) 4361–4366
4365
1
13
purified products were characterized by H and C NMR
and were in agreement with the reported values
[
2-Hydroxy-2-phenyl-propionitrile (derived from Table 3,
1
entry 1). H NMR (200 MHz, CDCl ): d = 1.84 (s, 3H),
3
1
3
13b,15,19b].
.3. Characterization data of product
-Hydroxy-2-phenylacetonitrile (derived from Table 1,
4.02 (br s, 1H), 7.35–7.92 (m, 5H); C NMR (50 MHz,
CDCl ): d = 31.1, 71.2, 115.1, 125.1, 129.0, 129.2, 129.7,
3
3
133.9 ppm. Elemental analysis. Anal. Calc. for C H NO:
9
9
C, 73.45; H, 6.16; N, 9.52. Found: C, 73.48; H, 6.13; N,
9.55%.
2
1
entry 3). H NMR (200 MHz, CDCl ): d = 4.14 (br s,
2-(2-chloro-phenyl)-2-hydroxy-propionitrile
1
(derived
from Table 3, entry 9). H NMR (200 MHz, CDCl ):
3
1
3
1
H), 5.44 (s, 1H), 7.35–7.43 (m, 5H);
50 MHz, CDCl ): d = 63.9, 119.8, 127.3, 129.7, 130.5,
C NMR
3
3
1
(
d = 1.99 (s, 3H), 4.29 (br s, 1H), 7.29–7.71 (m, 4H);
C
3
1
34.2, 135.9 ppm. Elemental analysis. Anal. Calc. for
NMR (50 MHz, CDCl ): d = 28.5, 69.1, 114.8, 121.2,
3
C H NO: C, 72.16; H, 5.30; N, 10.52. Found: C, 72.08;
127.2, 128.1, 130.9, 131.9, 137.4 ppm. Elemental analysis.
Anal. Calc. for C H ClNO: C, 59.52; H, 4.42; N, 7.71.
Found: C, 59.58; H, 4.40; N, 7.70%.
8
7
H, 5.32; N, 10.48%.
-Hydroxy-2-(4-ethoxyphenyl) acetonitrile (derived
9
8
2
1
from Table 2, entry 4) H NMR (200 MHz, CDCl3):
d = 1.47 (t, J = 7.2, 3H), 3.67 (br s, 1H), 4.14 (q, J = 6.0,
Acknowledgements
1
3
2
H), 5.54 (s, 1H), 6.94–7.42 (m, 4H);
C NMR
(
1
50 MHz, CDCl ): d = 15.4, 62.0, 65.1, 112.8, 115.1,
21.8, 131.9 ppm. Elemental analysis. Anal. Calc. for
3
N. H. Khan is thankful to DST and CSIR Network pro-
ject on Catalysis for financial assistance and also thankful
to Dr. P. K. Ghosh, the Director, of the Institute for pro-
viding instrumentation facility.
C H NO : C, 67.78; H, 6.26; N, 7.90. Found: C, 67.82:
H, 6.24; N, 7.88%.
1
0
11
2
0
2
-Hydroxy-2-(1 -naphthyl) acetonitrile (derived from
1
Table 2, entry 11) H NMR (200 MHz, CDCl ):d = 3.87
3
1
3
(
(
br s, 1H), 6.03 (s, 1H), 7.37–8.06 (m, 7H); C NMR
References
50 MHz, CDCl ): d = 62.7, 115.8, 119.5, 123.5, 125.7,
3
1
26.2, 127.1, 127.9, 129.6, 130.9, 131.4, 134.6 ppm. Elemen-
[1] (a) M. North, Synlett (1993) 807;
tal analysis. Anal. Calc. for C H NO: C, 78.67; H, 4.95;
(b) F. Effenberger, Angew. Chem. Int. Ed. Engl. 33 (1994) 1555;
1
2
9
(
c) M. North, in: A.R. Katritzky, O. Meth-Cohn, R.C. Wees, G.
N, 7.65. Found: C, 78.62; H, 5.02; N, 7.68%.
-Hydroxy-4-phenyl-butanenitrile (derived from Table 2,
Pattenden (Eds.), Comprehensive Organic Functional Group ‘Trans-
formations’, vol. 3, Pergamon Press, Oxford, 1995, Chapter 18;
2
1
entry 12) H NMR (200 MHz, CDCl ): d = 2.08–2.19 (m,
3
(
(
d) R.J.H. Gregory, Chem. Rev. 99 (1999) 3649;
e) J.M. Brunel, I.P. Holmes, Angew. Chem. Int. Ed. 43 (2004)
2
H), 2.78 (t, J = 7.6, 2H), 3.44 (br s, 1H), 4.36 (t,
1
3
J = 6.2, 1H), 7.17–7.33 (m, 5H); C NMR (50 MHz,
2752;
(
(
(
(
(
f) M. North, Tetrahedron: Asymmetry 14 (2003) 147;
g) M. Schmidt, S. Herve, N. Klempier, H. Griengl, Tetrahedron 52
1996) 7833;
h) A. Mori, H. Nitta, M. Kudo, S. Inous, Tetrahedron Lett. 32
1991) 4333;
CDCl ): d = 31.3, 37.2, 60.9, 115.1, 127.2, 129.1, 129.3,
3
1
40.3 ppm. Elemental analysis. Anal. Calc. for
C H NO: C, 74.51; H, 6.88; N, 8.69. Found: C, 74.55;
1
0
11
H, 6.84; N, 9.71%.
-Hydroxyheptanenitrile (derived from Table 2, entry
2
(i) H. Griengl, H. Schwab, M. Fechter, TIBTECH 18 (2000) 252;
j) A. Schmid, J.S. Dordick, B. Hauer, A. Kiener, M. Wubbolts, B.
Witholt, Nature (London) 409 (2001) 258;
k) H. Hirohara, M. ishizawa, Biosci. Biotechnol. Biochem. 62 (1998)
1
(
1
1
4). H NMR (200 MHz, CDCl ): d = 0.87–1.90 (m,
3
1H), 2.80 (br s, 1H), 4.50 (m, 1H); C NMR (50 MHz,
1
3
(
1
CDCl ): d = 14.5, 23.1, 24.9, 31.7, 35.9, 62.1, 115.1 ppm.
3
.
Elemental analysis. Anal. Calc. for C H NO: C, 66.10;
H, 10.30; N, 11.0. Found: C, 66.12, H; 10.26; N 11.02%.
7
13
[2] T. Kusumoto, T. Hanamoto, T. Hiyama, S. Takehera, T. Shoji, M.
Osawa, T. Kuriyama, K. Nakamura, T. Fujisawa, Chem. Lett. 19
(1990) 1615.
0
2
-Hydroxy-2-(2 -thiophen) acetonitrile (derived from
1
[3] (a) A. Lapworth, J. Chem. Soc. 83 (1903) 995;
Table 2, entry 16). H NMR (200 MHz, CDCl ):
d = 3.68 (br s, 1H), 5.72 (s, 1H), 7.05-7.42 (m, 3H);
3
(
b) W.C. Groutas, D. Felker, Synthesis (1980) 861, and references
1
3
C
cited therein;
NMR (50 MHz, CDCl ): d = 59.9, 115.1, 127.8, 128.0,
3
(c) A. Fujii, S. Sakaguchi, Y. Ishii, J. Org. Chem. 65 (2000) 6209;
(d) Y. Kawasaki, A. Fujii, Y. Nakano, S. Sakaguchi, Y. Ishii, J. Org.
Chem. 64 (1999) 4214.
4] S. Matsubara, T. Takai, K. Utimoto, Chem. Lett. (1991) 1447.
5] (a) Y. Yang, D. Wang, Synlett (1997) 861;
1
28.6 ppm. Elemental analysis. Anal. Calc. for C H NOS:
6 5
C, 51.78; H, 3.62; N, 10.06. Found: C, 51.82; H, 6.60; N,
0.01%.
E)-2-Hydroxy-4-phenyl-3-butenenitrile (derived from
[
[
1
(
(
b) Y. Yang, D. Wang, Synlett (1997) 1379.
1
Table 2, entry 18). H NMR (200 MHz, CDCl3):
d = 3.45 (br s, 1H), 5.13 (d, J = 5.6, 1H), 6.19 (dd,
J = 10.0, 5.8, 1H), 6.86 (d, J = 15.8, 1H), 7.32–7.39 (m,
[6] P. Saravanan, R.V. Anand, V.R. Singh, Tetrahedron Lett. 39 (1998)
3823.
[
7] P.G. Gassman, J.J. Talley, Tetrahedron Lett. 19 (1978) 3773.
[8] W.J. Greenlee, D.G. Hangauer, Tetrahedron Lett. 24 (1983)
559.
1
3
5
1
H); C NMR (50 MHz, CDCl ): d = 62.5, 114.9, 123.1,
3
4
27.7, 129.5, 129.7, 129.8, 135.8 ppm. Elemental analysis.
[
9] (a) G. Jenner, Tetrahedron Lett. 40 (1999) 491;
Anal. Calc. for C H NO; C, 75.45: H, 5.70; N, 8.80.
10
9
(b) N. Azizi, M.R. Saidi, J. Organomet. Chem. 688 (2003) 283.
Found: C, 75.42; H, 5.73; N, 8.78%.
[10] J.K. Whitesell, R. Apodaca, Tetrahedron Lett. 37 (1996) 2525.