6.19 (s, 1H, ArH), 7.08 (d, J=8.2 Hz, 2H, ArH), 7.23 (d, J=8.2 Hz, 2H, ArH), 10.68 (s, 1H, OH); 13 C NMR (63 MHz, CDCl3): δ = 15.2 (CH2CH3), 15.8 (CH3), 28.6 (CH2), 52.4 (OCH3), 52.8 (OCH3), 105.0 (C), 114.8 (ArCH), 122.3, 126.2 (C), 129.6 (2ArCH), 134.7 (C), 135.5 (2ArCH), 146.3, 150.2, 159.8, 169.2, 169.4 (C); IR (KBr, cm −1 ): v� = 3071 (w), 3021 (w), 2951 (w), 2873 (w), 1735 (s), 1667 (s), 1590 (s), 1562 (s), 1492 (m), 1430 (s), 1331 (s), 1278 (m), 1217 (s), 1125 (s), 1042 (s), 1004 (m), 939 (s), 827 (s), 802 (s), 743 (s); MS (EI, 70 eV): m/z (%) = 361 (22), 360 (M + , 100), 329 (27), 326 (26), 313 (17), 312 (12), 311 (56), 299 (29), 296 (39), 270 (10), 268 (10), 267 (26), 240 (12); HRMS (EI): calcd for C19H20O5S [M + ]: 360.10260, found: 360.101772. Cl S OH CO 2Me CO 2Me 3-Hydroxy-5-(4-chlorophenylsulfanyl)-phthalic acid dimethyl ester (14g): Starting with 3i (471mg, 1.5 mmol) and 13 (319 mg, 2.25 mmol), 14g was isolated as a highly viscous oil (338 mg, 64%); 1 H NMR (250 MHz, CDCl3): δ = 3.70 (s, 3 H, OCH3), 3.74 (s, 3 H, OCH3), 6.52-7.31 (m, 6H, ArH), 10.62 (s, 1H, OH); 13 C NMR (63 MHz, CDCl3): δ = 52.7 (OCH3), 52.8 (OCH3), 107.0 (C), 116.4, 117.2 (ArCH), 126.9, 128.7, (C), 130.1 (2ArCH), 135.9 (2ArCH), 147.3, 149.1, 161.5, 168.8, 168.9 (C); IR (KBr, cm −1 ): v = 3079 (w), 3044 (w), 3006 (w), 2955 (w), 2853 (w), 1727 (s), 1673 (s), 1594 (s), 1557 (s), 1475 (m), 1440 (s), 1434 (s), 1406 (m), 1388 (m), 1328 (s), 1265 (s), 1199 (s), 1164 (s), 1120 (s), 1016 (s), 934 (m), 852 (m), 802 (s), 773 (m), 744 (m), 703 (m), 636 (m), 586 (m), 567 (m); MS (EI, 70 eV): m/z (%) = 354 (M + , 35), 353 (16), 352 (M + , 100), 323 (12), 322 (12), 321 (48), 320 (20), 319 (42), 305 (19), 303 (44), 287 84
(13), 264 (13), 262 (36) ,260 (12), 234 (24), 171 (11); HRMS (EI): calcd for C16H13O5SCl [M + ]: 352.01667, found: 352.016164. Cl 3-Hydroxy-6-(4-chlorophenylsulfanyl)-4-methyl- phthalic acid dimethyl ester; (14h): Starting with 3j (492 mg, 1.5 mmol) and 13 (319 mg, 2.25 mmol), 14h was isolated as a highly viscous oil (302 mg, 55%); 1 H NMR (300 MHz, CDCl3): δ = 2.16 (s, 3H, CH3), 3.85 (s, 3 H, OCH3), 3.87 (s, 3 H, OCH3), 6.36-7.42 (m, 5H, ArH), 10.81 (s, 1H, OH); 13 C NMR (63 MHz, CDCl3): δ = 17.2 (CH3), 53.8 (OCH3), 54.0 (OCH3), 106.6 (C), 117.0 (ArCH), 124.1, 130.3, 130.5, 131.2 (C), 131.4, 137.3 (2ArCH), 149.5, 161.0, 170.2, 170.4 (C); IR (KBr, cm −1 ): v� = 3073 (w), 3025 (w), 2951 (w), 2873 (w), 1735 (s), 1667 (s), 1590 (s), 1562 (s), 1492 (m), 1430 (s), 1331 (s), 1278 (m), 1217 (s), 1128 (s), 1046 (s), 1004 (m), 945 (s), 827 (s), 802 (s), 747 (s); MS (EI, 70 eV): m/z (%) = 368 (M + , 39), 367 (19), 366 (M + , 100), 328 (17), 326 (26), 313 (17), 312 (12), 311 (56), 299 (29), 296 (39), 270 (10), 268 (10), 267 (26), 240 (13); HRMS (EI): calcd for C17H15O5SCl [M + ]: 366.03232, found: 366.031813. Cl S Me S OH OH CO 2Me CO 2Me CO 2Me CO 2Me 3-Hydroxy-5-(3-chlorophenylsulfanyl)-phthalic acid dimethyl ester (14i): Starting with 3k (471 mg, 1.5 mmol) and 13 (319 mg, 2.25 mmol), 14i 85
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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
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Table 2. Synthesis of thioxanthones
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3a O OSiMe 3 O OMe + Me Me Cl 3TiO
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Table 3. Synthesis of 8a-x 3 7 8 Ar
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Cl + SPh OSiMe 3 3a 9 O OMe O O H i
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solution. The use of an excess (1.5
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Table 4. Synthesis of 12a-r 3 11 12
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- Page 39 and 40: aromatization). An unseparable 1:2
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- 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 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
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- Page 69 and 70: S Methyl 4-methyl-5-(2-bromoethyl)-
- Page 71 and 72: (CH2CH3), 33.3 (CH2), 40.1 (CH2), 5
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- Page 77 and 78: OCH3), 7.08-7.17 (m, 7H, Ar); 13 C
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- Page 91 and 92: MS (EI, 70 eV): m/z (%) = 337 (16),
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- Page 95 and 96: Refrences 1. Handbook of Chemistry
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- Page 101 and 102: Publications 1. Inam Iqbal, Muhamma
- Page 103 and 104: Tetrahedron 2007, 63, 12562-12575.