241 (54), 240 (16), 239 (72), 226 (16), 225 (73), 198 (22), 197 (35), 165 (11), 121 (9), 105 (5), 77 (6); HRMS (EI): calcd for C16H16O2S [M + ]: 272.08655, found 272.086256. 3-(4-Chlorophenylsulfanyl)-biphenyl-4-benzoic acid methyl ester (12g). Starting with 3i (370 mg, 1.2 mmol), 11b (0.22 mL, 1.3 mmol), TiCl4 (0.2 mL, 1.7mmol) and CH2Cl2 (7 mL), 12g was isolated as a highly viscous oil (157 mg, 37%). 1 H NMR (250 MHz, CDCl3): δ = 3.53 (s, 3H, OCH3), 7.18-7.32 (m, 12H, Ar); 13 C NMR (63 MHz, CDCl3): δ = 52.1 (OCH3), 127.8, 128.2, 128.4, 129.0, 129.4, 130.1, 131.2, 132.8 (ArCH), 133.6, 133.6, 133.9, 135.7, 139.81, 141.1, 168.6 (C); IR (KBr, cm −1 ): v� = 3058 (w), 2996 (w), 2949 (w), 2927 (w), 2856 (w), 1729 (s), 1662 (w), 1574 (m), 1563 (m), 1459 (m), 1451 (m), 1435 (m), 1337 (w), 1267 (s), 1242 (s), 1189 (m), 1106 (s), 1067 (s), 955 (w), 773 (s), 678 (m), 663 (w); MS (EI, 70 eV): m/z (%) = 356 (M + , 37 Cl, 39), 354 (M + , 35 Cl, 100), 323 (36), 244 (15), 91 (7), 77 (5); HRMS (EI): calcd for C20H15O2ClS [M + ]: 354.06323, found: 354.063118. Cl Cl S S O Ph OMe O Me OMe 2-(3-Chlorophenylsulfanyl)-4-methyl-benzoic acid methyl ester (12h): Starting with 3k (470 mg, 1.5 mmol), 11a (0.23 mL, 2.25 mmol), TiCl4 (0.25 mL, 2.25 mmol) and CH2Cl2 (9 mL), 12h was isolated as a highly viscous oil (210 mg, 48%). 1 H NMR (250 MHz, CDCl3): δ = 2.28 (s, 3H, CH3), 3.79 (s, 3H, 72
OCH3), 7.08-7.17 (m, 7H, Ar); 13 C NMR (63 MHz, CDCl3): δ = 19.6 (CH3), 52.1 (OCH3), 126.9, 128.3, 129.6, 130.0, 130.1, 130.2, 131.2 (ArCH), 131.4, 134.7, 136.3, 137.7, 138.5 (C); IR (KBr, cm −1 ): v� = 3058 (w), 2996 (w), 2949 (w), 2927 (w), 2856 (w), 1729 (s), 1662 (w), 1574 (m), 1563 (m), 1459 (m), 1451 (m), 1435 (m), 1337 (w), 1267 (s), 1242 (s), 1189 (m), 1106 (s), 1067 (s), 955 (w), 773 (s), 678 (m), 663 (w); MS (EI, 70 eV): m/z (%) = 294 (M + , 37 Cl, 16), 292 (M + , 35 Cl, 71), 261 (71), 260 (18), 259 (100), 226 (15), 225 (37), 198 (16), 197 (29), 165 (8), 152 (6), 121 (9), 63 (5); HRMS (EI): calcd for C15H13O2SCl [M + , 35 Cl]: 292.03193, found 292.032372. F S O OMe Cl 4`-Chloro-3-(4-fluorophenylsulfanyl)-biphenyl-2-ArCboxylic acid methyl ester (12i). Starting with 3l (440 mg, 1.5 mmol), 11c (0.37 mL, 1.8 mmol), TiCl4 (0.25 mL, 2.25 mmol) and CH2Cl2 (9 mL), 12i was isolated as a colourless solid (195 mg, 35%). 1 H NMR (250 MHz, CDCl3): δ = 3.57 (s, 3H, OCH3), 6.99- 7.27 (m, 11H, Ar); 13 C NMR (75 MHz, CDCl3): δ = 51.2 (OCH3), 115.4, 115.7, 127.2 (ArCH), 127.6, 128.5,129.1, 129.2, 132.7, 133.7, 133.9 (ArCH), 134.4, 134.5, 136.6, 136.7, 137.3, 138.7, 167.4 (C); IR (KBr, cm −1 ): v� = 3091 (w), 3065 (w), 2992 (w), 2948 (w), 2851 (w), 1892 (w), 1711 (m), 1678 (m), 1587 (s), 1488 (s), 1445 (m), 1435 (m), 1397 (m), 1337 (m), 1272 (m), 1221 (s), 1193 (s), 1153 (s), 1105 (m), 1088 (s), 1012 (m), 898 (m), 829 (s), 813 (s), 790 (m), 733 (m), 637 (m); MS (EI, 70 eV): m/z (%) = 374 (M + , 37 Cl, 40), 372 (M + , 35 Cl, 100), 343 (16), 341 (42), 305 (14), 278 (16), 276 (20), 168 (8), 152 (6), 138 (9); HRMS (EI): calcd for C20H14O2ClFS [M + ]: 372.063816, found: 372.038069. 73
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Synthesis of functionalized 2-(aryl
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The ink of the scholar is more holy
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Affectionately Dedicated to “All
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Table of Contents 03 List of used a
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RCM Ring Closing Metathesis TBAI Te
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humans: 1) the thiomethyl of methio
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Chart 3. Structure of sumatriptan S
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disulfide (DADS) and diallyl sulfid
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1. Synthesis of functionalized 2-(a
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3-Arylthio-1-trimethylsilyloxy-1,3-
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under kinetic reaction control, by
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l a u 4-FC6H4 H Me H 40 m a v 4-FC6
- Page 25 and 26: Table 2. Synthesis of thioxanthones
- Page 27 and 28: 3a O OSiMe 3 O OMe + Me Me Cl 3TiO
- Page 29 and 30: Table 3. Synthesis of 8a-x 3 7 8 Ar
- Page 31 and 32: Cl + SPh OSiMe 3 3a 9 O OMe O O H i
- Page 33 and 34: solution. The use of an excess (1.5
- Page 35 and 36: Table 4. Synthesis of 12a-r 3 11 12
- Page 37 and 38: 2.3 Conclusion In conclusion, I hav
- Page 39 and 40: aromatization). An unseparable 1:2
- Page 41 and 42: Table 5. Synthesis of arenes 14a-l
- Page 43 and 44: 3.3 Conclusion In conclusion, I hav
- Page 45 and 46: Mass Spectroscopy: AMD MS40, AMD 40
- Page 47 and 48: 131.0 (ArCH), 132.7, 134.0, 135.9,
- Page 49 and 50: (EI, 70 eV): m/z (%): 380 (100), 21
- Page 51 and 52: (m), 1490 (m), 1434 (m), 1383 (w),
- Page 53 and 54: 15.4, 16.9, 18.9 (CH3), 28.3 (CH2),
- Page 55 and 56: (C). IR (neat): ν̃ = 2945 (w), 29
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- Page 59 and 60: 135.4, 139.2, 143.8, 146.5, 182.2 (
- Page 61 and 62: Me S O Me Ph Br Methyl 4-methyl-5-(
- Page 63 and 64: 35 Cl, 37 Cl, 61), 430 (M + , 35 Cl
- Page 65 and 66: ArH). 13 C NMR (62 MHz, CDCl3): δ
- Page 67 and 68: Me S O Me Me Methyl 4,6-dimethyl-5-
- Page 69 and 70: S Methyl 4-methyl-5-(2-bromoethyl)-
- Page 71 and 72: (CH2CH3), 33.3 (CH2), 40.1 (CH2), 5
- Page 73 and 74: Me 3,4-Dimethyl-2-phenylsulfanyl-be
- Page 75: Me 3,4-Dimethyl-2-(p-tolylsulfanyl)
- Page 79 and 80: (w), 750 (s), 732 (s), 688 (s), 650
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- Page 85 and 86: Me 3-Hydroxy-5-(4-methylphenylsulfa
- Page 87 and 88: Et 3-Hydroxy-5-(4-ethylphenylsulfan
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- Page 91 and 92: MS (EI, 70 eV): m/z (%) = 337 (16),
- Page 93 and 94: OH O 5'-Hydroxy-[1,1';3',1'']terphe
- Page 95 and 96: Refrences 1. Handbook of Chemistry
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- Page 99 and 100: Nationality Pakistan Place of Birth
- Page 101 and 102: Publications 1. Inam Iqbal, Muhamma
- Page 103 and 104: Tetrahedron 2007, 63, 12562-12575.