–1
9-Cyanononanoic Acid (6). R 0.45 (hexane–MTBE, 1:1). IR spectrum (KBr, ꢄ, cm ): 2220 (ÑN), 1700 (CO Í).
f
2
1
Í NMR spectrum (300 MHz, CDCl , ꢅ, ppm, J/Hz): 1.29–1.64 (12Í, m, ÑÍ -3ꢆÑÍ -8), 2.33 (2Í, m, ÑÍ -2), 2.41 (2Í, m,
3
2
2
2
13
ÑÍ -9), 10.20 (1Í, br.s, ÎÍ). C NMR spectrum (75.47 MHz, CDCl , ꢇꢅ, ppm): 18.02 (t, Ñ-9), 25.06 (t, Ñ-3), 25.25 (t, Ñ-8),
2
3
28.31 (t, Ñ-7), 29.04 (t, Ñ-5ꢆÑ-6), 29.22 (t, Ñ-4), 34.40 (t, Ñ-2), 119.12 (s, ÑN), 180.00 (s, ÑO H).
2
Ozonolysis in AcOH. Method a) after chromatography of the residue (1.89 g) (SiO , hexane–MTBE, 4:1) afforded
2
sebacic acid (7, 1.70 g, 77%) and oxime acid 8 (0.19 g, 9%); method b), 7 (1.83 g, 83%).
–1
1,10-Decanedioic Acid (7). R 0.35 (hexane–MTBE, 1:1), mp 130–132°C. IR spectrum (KBr, ꢄ, cm ): 3180,
f
13
1703(CO H). The PMR and C NMR spectra were identical to those published [14].
2
–1
10-(Hydroxyimino)decanoic Acid (8). R 0.30 (hexane–MTBE, 1:1). IR spectrum (KBr, ꢄ, cm ): 1700 (CO Í),
f
2
1
1647 (C=N). Í NMR spectrum (300 MHz, CDCl , ꢅ, ppm, J/Hz): 1.34–1.49 (10Í, m, ÑÍ -4ꢆÑÍ -7), 1.54–1.62 (2Í, m,
3
2
2
13
ÑÍ -3), 1.65 (2Í, m, ÑÍ -8), 2.19 (2Í, m, ÑÍ -9), 2.31 (2Í, t, ÑÍ -2), 7.20 (t, ÑÍ-10), 10.50 (2Í, br.s, 2ÎÍ). C NMR
2
2
2
2
spectrum (75.47 MHz, CDCl , ꢅ, ppm): 17.06 (t, Ñ-9), 25.81 (t, Ñ-3), 26.23 (t, Ñ-8), 28.53 (t, Ñ-4ꢆÑ-7), 34.05 (t, Ñ-2), 151.53
3
(d, ÑÍNOH), 180.00 (s, ÑO H).
2
Ozonolysis in AcOH–H O. Method a) after chromatography of the residue (1.97 g) (SiO , hexane–MTBE, 4:1)
2
2
afforded sebacic acid (7, 0.58 g, 26%) and oxime acid 8 (1.20 g, 55%); method b), 7 (1.32 g, 60%).
Ozonolysis in CH Cl . Method a) afforded 7 (1.54 g, 70%); method b) after chromatography of the residue (1.88 g)
2
2
(SiO , hexane–MTBE, 4:1), 7 (1.13 g, 51%) and aldehyde acid 11 (0.75 g, 37%).
2
–1
1
10-Oxodecanoic Acid (11) [11]. IR spectrum (KBr, ꢄ, cm ): 1718 (Ñ=Î), 1700 (CO Í). Í NMR spectrum
2
(300 MHz, CDCl , ꢅ, ppm, J/Hz): 1.27–1.59 (12Í, m, ÑÍ -3ꢆÑÍ -8), 2.31 (2Í, m, ÑÍ -2), 2.40 (2Í, m, ÑÍ -9), 9.80 (1Í,
3
2
2
2
2
13
br.s, Ñ(Î)Í-10), 10.2 (1Í, br.s, ÎÍ). C NMR spectrum (75.47 MHz, CDCl , ꢅ, ppm): 22.05 (t, Ñ-8), 25.06 (t, Ñ-3), 28.86 (t,
3
Ñ-7), 29.05 (t, Ñ-5ꢆÑ-6), 29.22 (t, Ñ-4), 34.01 (t, Ñ-2), 44.03 (t, Ñ-9), 180.00 (s, ÑO H), 202.02 (d, Ñ=O).
2
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