List of used abbreviations - RosDok - Universität Rostock

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S OH 3-Hydroxy-5-(2-naphthyl)sulfanyl-phthalic acid dimethyl ester (14l): Starting with 3p (496 mg, 1.5 mmol) and 13 (319 mg, 2.25 mmol), 14l was isolated as a highly viscous oil (298 mg, 54%); 1 H NMR (250 MHz, CDCl3): δ = 3.68 (s, 3 H, OCH3), 3.72 (s, 3 H, OCH3), 6.56-7.92 (m, 8H, ArH), 10.60 (s, 1H, OH); 13 C NMR (63 MHz, CDCl3): δ = 52.6 (OCH3), 52.8 (OCH3), 106.6 (C), 116.4, 117.2 (ArCH), 127.2 (C), 127.3, 127.8, 127.9, 129.7, 130.9 (ArCH), 133.3, 133.8 (C), 134.7, 134.9 (ArCH), 135.8, 148.1, 161.5, 168.9, 169.0 (C); IR (neat): ν̃ = 3052 (w), 2999 (w), 2949 (w), 2840 (w), 1731 (s), 1666 (s), 1595 (s), 1555 (s), 1497 (m), 1434 (s), 1400 (m), 1330 (s), 1264 (s), 1196 (s), 1167 (s), 1119 (s), 1016 (s), 934 (s), 850 (s), 802 (s), 742 (s), 646 (m); MS (EI, 70 eV): m/z (%) = 369 (19), 368 (M + , 100), 337 (11), 335 (17), 319 (24), 303 (18), 250 (19), 248 (10), 221 (12); HRMS (EI): calcd for C20H16O5S [M + ]: 368.07130, found: 368.071809. General procedure for the synthesis of 17a-c: To a dichloromethane solution (10 mL / mmol of 15) of 15 (1.65 mmol) and of 16 (1.5 mmol) was added TiCl4 (1.5 mmol) at –78 °C. The solution was allowed to warm to 20 °C within 20 h. To the solution was added a saturated aqueous solution of 10% HCl (15 mL). The organic and the aqueous layer were separated and the latter was extracted with CH2Cl2 (3 x 20 mL). The combined organic layers were dried (Na2SO4), filtered, and the filtrate was concentrated in vacuo. The residue was purified by chromatography (silica gel, EtOAc / n-heptane = 1:4). CO 2Me CO 2Me 88
OH O 5'-Hydroxy-[1,1';3',1'']terphenyl-4'-carboxylic acid methyl ester (17a): Starting with 15 (430mg, 1.65 mmol), 16a (444mg, 1.5 mmol), TiCl4 (0.2ml, 1.65 mmol) and CH2Cl2 (9ml), 17a was isolated as a gummy compound (201 mg, 40%); 1 H NMR (300 MHz, CDCl3): δ = 3.40 (s, 3H, OCH3), 6.96-7.54 (m, 12H, ArH), 10.75 (s, 1H, OH); 13 C NMR (75 MHz, CDCl3): δ = 52.1 (OCH3), 111.1, 115.1, 122.0, 127.3 (ArCH), 127.6, 128.0, 128.5 (2C ArCH), 128.9 (ArCH), 129.3 (2C ArCH), 139.7, 143.2, 145.8, 146.8, 162.3 (ArCH), 171.7 (C); IR (neat): ν̃ = 3426 (m), 3083 (w), 3054 (m), 3025 (m), 2947 (m), 1664 (s), 1597 (m), 1553 (m), 1491 (w), 1437 (s), 1386 (s), 1354 (m), 1319 (s), 1256 (s), 1230 (s), 1198 (m),. 1142 (s), 1014 (m), 776 (m), 767 (m), 702 (s); cm−1; GC-MS (EI, 70 eV): m/z (%): 304 (40), 273 (23), 272 (M + , 100), 245 (9), 244 (38), 216 (11), 215 (54), 213 (8), 202 (3), 189 (3), 152 (5), 139 (3), 122 (6), 113 (4), 107 (16), 94 (7). HRMS (EI): calcd for C20H16O3 [M + ]: 304.10940, found 304.109762. OH O OMe Me 1-(5'-Hydroxy-[1,1';3',1'']terphenyl-4'-yl)-ethanone) (17b): Starting with 15 (403mg, 1.65 mmol), 16b ( 444mg, 1.5 mmol), TiCl4 (0.2ml, 1.65 mmol) and CH2Cl2 (9ml), 17b was isolated as a gummy compound (194mg, 41%); 1 H NMR (300 MHz, CDCl3): δ = 1.80 (s, 3H, CH3), 6.79-7.93 (m, 12H, ArH), 11.87 (s, 1H, OH); 13 C NMR (75 MHz, CDCl3): δ = 28.6 (CH3), 114.1, 116.3, 118.8, 120.3, 122.4(ArCH), 126.2 (2C ArCH), 127.7 (ArCH), 127.9 (2C ArCH), 131.4, 134.5, 138.2, 142.2, 144.3 145.6, 160.8, 184.7 (ArCH), 205.6 (C); IR (neat): ν̃ = 3425 (m), 3086 (w), 3054 (m), 3025 (m), 2946 (m), 1665 (s), 1596 (m), 1554 (m), 89
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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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2.3 Conclusion In conclusion, I hav
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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
Page 57 and 58: 948 (w) 853 (m), 803 (m), 751 (m),
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 and 76: Me 3,4-Dimethyl-2-(p-tolylsulfanyl)
Page 77 and 78: OCH3), 7.08-7.17 (m, 7H, Ar); 13 C
Page 79 and 80: (w), 750 (s), 732 (s), 688 (s), 650
Page 81 and 82: 35 Cl 35 Cl, 100), 359 (26), 357 (3
Page 83 and 84: 2924 (w), 2853 (w), 1728 (s), 1712
Page 85 and 86: Me 3-Hydroxy-5-(4-methylphenylsulfa
Page 87 and 88: Et 3-Hydroxy-5-(4-ethylphenylsulfan
Page 89 and 90: (13), 264 (13), 262 (36) ,260 (12),
Page 91: MS (EI, 70 eV): m/z (%) = 337 (16),
Page 95 and 96: Refrences 1. Handbook of Chemistry
Page 97 and 98: 20. For a review of [3+3] cyclizati
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.
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List of used abbreviations - RosDok - Universität Rostock

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