(R)- and (S)-Ketone cyanohydrins
2-Hydroxy-2-ethyl-2-phenylacetonitrile C1oH11NO 2g
1557
IH NMR (CDCI3): 8 1.04 (t, 3H, CH3); 1.98-2.18 (qq, 2H, CH2); 2.90 (s, IH, OH); 7.37-7.45
(m, 3H, Harom); 7.55-7.58 (m, 2H, Harom); 13C NMR (CDCI3): 8 8.79 and 36.89 (CH3); 75.48 (C);
120.71 (CN); 2"125.07, 2"128.96, 129.29 and 139.78 (Carom). MS: rn/z 161 (M, 20), 132 (100), 105
(40), 77 (30), 51 (20) and 39 (6).
2-Hydroxy'-2-(dichloromethyl)-2-phenylacetonitrile C9H7CI2NO 2h
IH NMR (CDCI3): 8 3.94 (s, H, OH); 5.79 (s, IH, CH); 7.45-7.50 (m, 3H, Harom); 7.66-7.68 (m,
2H, Harom); 13C NMR (CDCI3): 8 22.86 (CH); 76.01 (C); 126.41 (CN); 128.95, 130.67, 133.79 and
138.50 (Carom). MS: m/z 219 (M+I, 0. l), 217 (M-I, 0.5), 215 (M-3, 1.0), 163 (0.5), 144 (1), 132
(45), 125 (5), 105 (100), 77 (50), 51 (26) and 39 (5).
2-Hydroxy- 2,5-dimethyl hexanenitrile CsHI5NO 2i
IH NMR (CDCI3): 8 0.95 (d, 6H, CH3); 1.10-1.90 (m, 7H); 1.61 (s, 3H, CH3); 13C NMR (CDCI3):
8 22.42 (2"CH3); 27.72, 27.95, 33.05, 39.72 (CH2) 68.86 (C), 121.96 (CN). MS: m/z 140 ( M - l ,
0.3), 126 (3), 108 (10), 99 (12), 83 (5), 81 (14), 71 (100), 58 (34), 56 (54), 43 (88) and 41 (6).
Acknowledgements
We thank the Technology Development Centre (TEKES) for financial support.
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(Received in UK 24 February 1997)