10.1002/ejoc.201800111
European Journal of Organic Chemistry
10
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(RS)-N-(tert-Butanesulfinyl)-3-(4-methoxyphenyl)propan-1-imine (4h): Colourless oil; [α]D -140 (c 1,
CH2Cl2); Rf 0.70 (hexane/EtOAc: 1/1); IR ν (film) 2956, 2931, 2825, 1612, 1510, 1462, 1363, 1244, 1177, 1082,
821 cm-1; δH 8.10 (t, J = 4.2 Hz, 1H), 7.12 (dd, J = 8.7, 0.6 Hz, 2H), 6.83 (dd, J = 8.8, 0.6 Hz, 2H), 3.78 (s, 3H),
2.94-2.89 (m, 2H), 2.85-2.79 (m, 2H), 1.14 (s, 9H); δC 168.8 (CH), 158.1, 132.45 (C), 129.4, 114.1 (CH), 56.8
(C), 55.4 (CH3), 37.9, 30.7 (CH2), 22.4 (CH3); LRMS (EI) m/z 211 (M+-C4H8, 17%), 162 (14), 121 (100), 57 (45),
41 (10); HRMS (ESI): Calculated for C14H21NO2S (M+) 267.1293, found 267.1303.
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(RS)-N-(tert-Butanesulfinyl)-4-phenylbutan-1-imine (4i): Colourless oil; [α]D -54 (c 0.5, CH2Cl2); Rf 0.78
(hexane/EtOAc: 1/1); IR ν (film) 3028, 2925, 2849, 1622, 1582, 1421, 1371, 1264, 1155, 1076 cm-1; δH 8.09 (t, J
= 4.4 Hz, 1H), 7.31-7.26 (m, 5H), 2.71-2.67 (m, 2H), 2.57-2.52 (m, 2H), 1.98-1.95 (m, 2H), 1.20 (s, 9H); δC
169.25 (CH), 141.4 (C), 128.6, 128.3, 126.05 (CH), 56.6 (C), 35.5, 29.7, 27.1 (CH2), 22.4 (CH3); LRMS (EI) m/z
145 (M+-C4H10SO, 19%), 105 (100), 103 (12), 79 (10), 77 (15); HRMS (ESI): Calculated for C14H21NOS (M+)
251.1344, found 251.1341.
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(RS)-N-(tert-Butanesulfinyl)-4-(2-methylphenyl)butan-1-imine (4j): Colourless oil; [α]D -111 (c 1, CH2Cl2);
Rf 0.78 (hexane/EtOAc: 1/1); IR ν (film) 3026, 2953, 2866, 1620, 1456, 1378, 1362, 1183, 1160, 1080, 740 cm-1;
δH 8.13 (t, J = 4.5 Hz, 1H), 7.28-7.12 (m, 4H), 2.73-2.68 (m, 2H), 2.65-2.58 (m, 2H), 2.33 (s, 3H), 1.99-1.91 (m,
2H), 1.22 (s, 9H); δC 169.3 (CH), 139.6, 135.85 (C), 130.3, 128.9, 126.2, 126.0 (CH), 56.6 (C), 35.9, 32.7, 25.8
(CH2), 22.4, 19.3 (CH3); LRMS (EI) m/z 159 (M+-C4H10SO, 40%), 118 (21), 117 (18), 106 (30), 105 (100), 91
(20), 79 (10), 77 (13); HRMS (ESI): Calculated for C15H23NOS (M+) 265.1500, found 265.1489.
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(RS)-N-(tert-Butanesulfinyl)-4-(4-methylphenyl)butan-1-imine (4k): Colourless oil; [α]D -267 (c 0.5,
CH2Cl2); Rf 0.80 (hexane/EtOAc: 1/1); IR ν (film) 3050, 2960, 2926, 2830, 1622, 1514, 1456, 1421, 1364, 1265,
1073, 964 cm-1; δH 8.11 (t, J = 4.5 Hz, 1H), 7.12-7.08 (m, 4H), 2.69-2.65 (m, 2H), 2.57-2.54 (m, 2H), 2.34 (s,
3H), 1.98-1.92 (m, 2H), 1.22 (s, 9H); δC 169.3 (CH), 138.3, 135.5 (C), 129.1, 128.3 (CH), 56.55 (C), 35.5, 34.8,
27.2 (CH2), 22.4, 21.0 (CH3); LRMS (EI) m/z 159 (M+-C4H10SO, 71%), 118 (30), 117 (14), 106 (21), 105 (100),
91 (15), 77 (15); HRMS (ESI): Calculated for C15H23NOS (M+) 265.1500, found 265.1508.
(RS)-N-(tert-Butanesulfinyl)-4-(2-bromophenyl)butan-1-imine (4l):[8d] Colourless oil; [α]D23 -94 (c 1, CH2Cl2);
Rf 0.78 (hexane/EtOAc: 1/1); IR ν (film) 3052, 2957, 2923, 2875, 1621, 1514, 1455, 1362, 1182, 1085, 807 cm-1;
δH 8.11 (t, J = 4.5 Hz, 1H), 7.53 (dd, J = 9.5, 1.5 Hz, 1H), 7.24-7.22 (m , 2H), 7.07 (ddd, J = 10.1, 6.7, 2.7 Hz,
1H), 2.83-2.79 (m, 2H), 2.62-2.57 (m, 2H), 1.99-1.95 (m, 2H), 1.20 (s, 9H); δC 169.1 (CH), 140.8 (C), 133.0,
130.4, 127.9, 127.6 (CH), 124.5, 56.7 (C), 35.65 , 35.6, 25.6 (CH2), 22.5 (CH3); LRMS (EI) m/z 225 (M+-C4H8-
81Br, 30%), 223 (31), 185 (18), 184 (18), 183 (19), 182 (17), 171 (96), 170 (10), 169 (100), 144 (39), 116 (11),
115 (11), 104 (11), 103 (13), 91 (14), 90 (27), 89 (27), 77 (16), 63 (14), 51 (12).
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