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m/z (%): 254 (100), 239 (46), 225 (34), 211 (12), 178 (13), 165 (15), 91 (8). HRMS (EI): calcd for C16H14OS [M + ]: 254.07799, found 254.07586. S Me Me Cl 2-Chloro-1,3-dimethylthioxanthone (6b): Starting with 5c (114 mg, 0.4 mmol) and conc. sulfuric acid, 6b was isolated as a highly viscous oil (114 mg, 97%). 1 H NMR (250 MHz, CDCl3): δ = 2.38 (s, 3 H, CH3), 2.83 (s, 3 H, CH3), 7.16 (s, 1 H, ArH), 7.45 (m, 3 H, ArH), 8.31 (dd, 1 H, 3 J = 7.9, 4 J = 2.0 Hz, ArH). 13 C NMR (62 MHz, CDCl3): δ = 19.8, 21.4 (CH3), 125.1 (2C, ArCH), 126.2 (ArCH), 127.3 (C), 129.6, 131.7 (ArCH), 131.8, 135.0, 135.3, 136.7, 141.7, 141.9, 182.4 (C). IR (neat): ν̃ = 3375 (w), 2978 (s), 1734 (m), 1675 (m), 1590 (m), 1490 (m), 1319 (m), 1219 (m), 1176 (m), 1029 (m), 751 (w) 690 (m) cm −1 . GC-MS (EI, 70 eV): m/z (%): 276 (M + , 37 Cl, 37), 274 (M + , 35 Cl, 41), 267 (100), 105 (89), 77 (34). HRMS (EI): calcd for C15H11OClS [M + , 35 Cl]: 274.06127, found 274.06139. S O O Me nPr 1-Propyl-3-methylthioxanthone (6c): Starting with 5e (50 mg, 0.16 mmol) and conc. sulfuric acid, 6c was isolated as a highly viscous oil (42 mg, 95%). 1 H NMR (250 MHz, CDCl3): δ = 0.90 (t, 3 H, J = 7.4, CH3), 1.60 (m, 2 H, CH2), 2.55 (t, H, J = 7.4, CH2), 2.81 (m, 3 H, CH3), 7.10 (S, 1 H, ArH), 7.38 (m, 3 H, ArH), 8.25 (dd, 1 H, 3 J = 7.2, 4 J =1.87 Hz, ArH). 13 C NMR (62 MHz, CDCl3): δ = 13.8, 23.4 (CH3), 24.8, 37.6 (CH2), 123.6, 125.1, 125.9 (ArCH), 127.2 (C), 129.6, 131.0, 131.5 (ArCH), 132.1, 54
135.4, 139.2, 143.8, 146.5, 182.2 (C). IR (neat): ν̃ = 3056 (w), 2973 (w), 1732 (m), 1625 (s), 1560 (m), 1460 (s), 1329 (s), 1249 (2), 1186 (s), 1029 (m), 723 (w) 690 (m) cm −1 . GC-MS (EI, 70 eV): m/z (%): 268 (100), 253 (7), 239 (34), 211 (36), 178 (10), 120 (7), 77 (8). HRMS (EI): calcd for C17H16OS [M + ]: 268.09164, found 268.09153. General procedure for the synthesis of diaryl sulfides 8a-x: To a dichloromethane solution (30 mL/mmol) of 3-arylthio-1-trimethylsilyloxy-1,3- butadienes 3 (1.0 mmol) and 1,1-diacyclopropane 7 (1.5 mmol) was added TiX4 (1.5 mmol, X = Cl, Br) at –78 °C. The solution was allowed to warm to ambient temperature within 14 h. To the solution was added a diluted aqueous solution of HCL (25 mL). The organic and the aqueous layer were separated and the latter was extracted with dichloromethane (3 x 20 mL). The filtrate was concentrated in vacuo and the residue was purified by chromatography (silica gel, EtOAc / n-heptane ). Me S O Me Me Cl OMe Methyl 4,6-dimethyl-5-(2-chloroethyl)-2-(4-methylphenyl- sulfanyl)benzoate (8h): Starting with 7a (283 mg, 2.25 mmol) 3d (441 mg, 1.5 mmol), TiCl4 (0.25 mL, 2.25 mmol) and CH2Cl2 (45 mL), 8h was isolated as a highly viscous oil (208 mg, 40%). 1 H NMR (250 MHz, CDCl3): δ = 2.18 (s, 3 H, CH3), 2.21 (s, 3 H, CH3), 2.22 (s, 3 H, CH3), 3.03 (t, J=8.3 Hz, 2 H, CH2), 3.44 (t, J=8.3 Hz, 2 H, CH2), 3.78 (s, 3 H, OCH3), 6.93-7.07 (m, 5 H, ArH). 13 C NMR (62 MHz, CDCl3): δ = 16.8, (CH3), 20.1 (CH3), 21.3 (CH3), 33.1 (CH2), 41.6 55
Page 1 and 2:
Synthesis of functionalized 2-(aryl
Page 3 and 4:
The ink of the scholar is more holy
Page 5 and 6:
Affectionately Dedicated to “All
Page 7 and 8: Table of Contents 03 List of used a
Page 9 and 10: RCM Ring Closing Metathesis TBAI Te
Page 11 and 12: humans: 1) the thiomethyl of methio
Page 13 and 14: Chart 3. Structure of sumatriptan S
Page 15 and 16: disulfide (DADS) and diallyl sulfid
Page 17 and 18: 1. Synthesis of functionalized 2-(a
Page 19 and 20: 3-Arylthio-1-trimethylsilyloxy-1,3-
Page 21 and 22: under kinetic reaction control, by
Page 23 and 24: 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
Page 57: 948 (w) 853 (m), 803 (m), 751 (m),
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 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
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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