Page 13 of 29
The Journal of Organic Chemistry
140.3, 133.1, 129.5, 129.1, 128.5, 128.4, 127.8, 126.7, 49.0, 34.6, 29.8, 22.4; ATR-FTIR (cm-1): 1739, 1599, 1450, 1266, 710; HRMS
m/z (ESI) calcd for C18H18NO2 (M + H)+ 280.1332, found 280.1336.
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2-(4-(tert-Butyl)phenyl)cyclopentan-1-one O-benzoyl oxime (1j). A white soild, mp 102-104 oC (5.0 mmol scale, 838.5 mg, 50%):
1H NMR (400 MHz, CDCl3) δ 8.07 – 8.05 (m, 1H), 7.58 – 7.41 (m, 2H), 7.37 – 7.32 (m, 3H), 7.27 – 7.19 (m, 2H), 7.14 – 7.12 (m,
1H), 4.07 – 4.03 (m, 1H), 2.97 – 2.75 (m, 2H), 2.44 – 2.26 (m, 1H), 2.09 – 1.74 (m, 3H), 1.30 – 1.29 (m, 9H); 13C NMR (101 MHz,
CDCl3) δ 177.8, 175.9, 163.9, 163.8, 149.5, 149.4, 138.6, 137.2, 133.1, 132.8, 129.54, 129.49, 129.3, 128.8, 128.4, 128.0, 127.5,
126.8, 125.6, 125.5, 48.6, 48.3, 36.7, 34.5, 34.4, 33.1, 31.4 31.3, 29.9, 23.8, 22.5; ATR-FTIR (cm -1): 1739, 1650, 1550, 1454, 1260,
712; HRMS m/z (ESI) calcd for C22H25NNaO2 (M + Na)+ 358.1778, found 358.1780.
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2-(4-Fluorophenyl)cyclopentan-1-one O-benzoyl oxime (1k). A white soild, mp 85-87 oC (5.0 mmol scale, 628.2 mg, 42%): 1H
NMR (400 MHz, CDCl3) δ 8.07 – 8.05 (m, 2H), 7.60 – 7.56 (m, 1H), 7.46 (t, J = 7.7 Hz, 2H), 7.31 – 7.28 (m, 2H), 7.04 – 7.00 (m,
2H), 4.02 (t, J = 7.6 Hz, 1H), 2.99 – 2.74 (m, 2H), 2.36 – 2.29 (m, 1H), 2.04 – 1.81 (m, 3H); 13C NMR (101 MHz, CDCl3) δ 177.3,
163.8, 161.71 (d, J = 245.0 Hz), 135.9 (d, J = 2.8 Hz), 133.2, 129.5, 129.4 (d, J = 8.0 Hz), 129.1, 128.5, 115.4 (d, J = 21.4 Hz), 48.5,
34.8, 29.8, 22.4; 19F NMR (376 MHz, CDCl3) δ -116.3; ATR-FTIR (cm -1): 2245, 1738, 1644, 1495, 1454, 1266, 708; HRMS m/z
(ESI) calcd for C18H16FNNaO2 (M + Na)+ 320.1057, found 320.1060.
2-([1,1'-Biphenyl]-4-yl)cyclopentan-1-one O-benzoyl oxime (1l). A white soild, mp 134-136 oC (5.0 mmol scale, 837.8 mg, 47%):
1H NMR (400 MHz, CDCl3) δ 8.08 (d, J = 8.1 Hz, 1H), 7.61 – 7.40 (m, 10H), 7.36 – 7.33 (m, 1H), 7.28 (d, J = 8.2 Hz, 1H), 7.21 –
7.17 (m, 1H), 4.18 – 4.09 (m, 1H), 3.00 – 2.79 (m, 2H), 2.50 – 2.32 (m, 1H), 2.14 – 1.80 (m, 3H); 13C NMR (101 MHz, CDCl3) δ
177.6, 175.5, 163.9, 163.8, 140.9, 140.8, 140.7, 139.7, 139.5, 139.4, 133.2, 132.9, 129.6, 129.5, 128.8, 128.7, 128.5, 128.3, 128.1,
127.6, 127.5, 127.3, 127.2, 127.1, 127.0, 126.9, 48.9, 48.4, 36.7, 34.7, 33.1, 29.9, 23.8, 22.5; ATR-FTIR (cm -1): 1742, 1732, 1654,
1501, 1454, 1266, 708; HRMS m/z (ESI) calcd for C24H22NO2 (M + H)+ 356.1645, found 356.1650.
2-(4-Methoxyphenyl)cyclopentan-1-one O-benzoyl oxime (1m). A white soild, mp 125-127 oC (5.0 mmol scale, 821.5 mg, 53%):
1H NMR (400 MHz, CDCl3) δ 8.06 (d, J = 7.4 Hz, 1.51H), 7.58 (t, J = 7.3 Hz, 1H), 7.46 (t, J = 7.6 Hz, 2H), 7.26 – 7.24 (m, 2H), 7.12
(d, J = 8.5 Hz, 0.5H), 6.88 – 6.84 (m, 2H), 4.10 – 3.99 (m, 1H), 3.79 (s, 3H), 2.94 – 2.76 (m, 2H), 2.37 – 2.27 (m, 1H), 2.04 – 1.80
(m, 3H); 13C NMR (101 MHz, CDCl3) δ 177.7, 175.9, 163.8, 158.4, 158.2, 133.8, 133.1, 132.9, 132.2, 129.52, 129.45, 129.2, 128.8,
128.4, 128.11, 128.09, 114.1, 114.0, 55.3, 55.2, 48.4, 47.7, 36.7, 34.6, 32.9, 29.8, 23.6, 22.4; ATR-FTIR (cm -1): 1740, 1640, 1451,
1263, 708; HRMS m/z (ESI) calcd for C19H20NO3 (M + H)+ 310.1438, found 310.1441.
2-(Naphthalen-2-yl)cyclopentan-1-one O-benzoyl oxime (1n). A white soild, mp 130-132 oC (5.0 mmol scale, 958.6 mg, 58%):
1H NMR (400 MHz, CDCl3) δ 8.09 – 8.07 (m, 1H), 7.84 – 7.78 (m, 3H), 7.75 – 7.68 (m, 1H), 7.61 – 7.42 (m, 4H), 7.34 – 7.28 (m,
1H), 7.24 – 7.22 (m, 1H), 6.96 – 6.93 (m, 1H), 4.30 – 4.22 (m, 1H), 3.03 – 2.83 (m, 2H), 2.51 – 2.34 (m, 1H), 2.21 – 1.81 (m, 3H);
13C NMR (101 MHz, CDCl3) δ 177.4, 175.4, 163.84, 163.77, 139.1, 137.7, 133.5, 133.4, 133.1, 132.8, 132.4, 132.1, 129.6, 129.3,
129.2, 128.7, 128.51, 128.45, 128.3, 127.9, 127.8, 127.6, 127.52, 127.47, 126.4, 126.3, 126.1, 126.0, 125.7, 125.6, 125.4, 36.6, 34.5,
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