List of used abbreviations - RosDok - Universität Rostock

More documents

Recommendations

Info

All reactions were carried out under an inert atmosphere, oxygen and humidity exclusion. All of the chemicals are standard, commercially available from Merck®, Aldrich®, Acros® and others. The order of the characterized connections effected numerically, but does not correspond to the order in the main part of dissertation. General procedure for the synthesis of 2-(thiophenoxy)benzoates 5a-v: To a dichloromethane solution (5 mL / mmol of 3) of 3 (1.0 mmol) and of 4 (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 NaHCO3 (15 mL). The organic and the aqueous layer were separated and the latter was extracted with diethyl ether (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). Me S O Me OMe 2,4-Dimethyl-6-phenylsulfanyl-benzoic acid methyl ester (5a): Starting with 4a (387 mg, 2.3 mmol), 3a (420 mg, 1.5 mmol), TiCl4 (0.25 mL, 2.3 mmol) and CH2Cl2 (9 mL), 5a was isolated as a highly viscous oil (229 mg, 56%). 1 H NMR (250 MHz, CDCl3): δ = 2.05 (s, 3H, CH3), 2.13 (s, 3H, CH3), 3.67 (s, 3H, OCH3), 6.75-7.12 (m, 7H, ArH). 13 C NMR (63 MHz, CDCl3): δ = 19.6, 21.1 (CH3), 52.0 (OCH3), 126.9 (ArCH), 129.0 (2C ArCH), 130.4 (ArCH), 130.8 (2C ArCH), 42
131.0 (ArCH), 132.7, 134.0, 135.9, 136.1, 140.7 (ArC), 169.1 (C). IR (neat): ν̃ = 3056 (w), 2990 (w), 2947 (w), 2920 (w), 1726 (s), 1599 (m), 1581 (w), 1516 (w), 1476 (m), 1438 (s), 1378 (w), 1267 (s), 1257 (s), 1217 (m), 1188 (m), 1151 (s), 1078 (s), 1023 (m), 999 (w), 956 (w) 852 (m), 810 (m), 738 (s), 689(s) 579 (m), 555 (w) cm −1 . GC- MS (EI, 70 eV): m/z (%): 272 (60), 241 (41), 240 (21), 239 (M + , 100), 198 (15), 197 (26), 165 (6), 91 (4). HRMS (EI): calcd for C16H16O2S [M + ]: 272.08655, found 272.086221. Methyl 2,3,4-trimethyl-6-(phenylsulfanyl)benzoate (5b): Starting with 4b (558 mg, 3.0 mmol), 3a (562 g, 2.0 mmol), TiCl4 (0.32 mL, 3.0 mmol) and CH2Cl2 (10 mL), 5b was isolated as a yellow highly viscous oil (250 mg, 43%). 1 S O OMe H Me Me Me NMR (250 MHz, CDCl3): δ = 2.00 (s, 3 H, CH3), 2.04 (s, 3 H, CH3), 2.05 (s, 3 H, CH3), 3.65 (s, 3 H, OCH3), 6.76 (s, 1 H, ArH), 7.0 (m, 2 H, ArH), 7.06 (m, 2 H, ArH). 13 C NMR (62 MHz, CDCl3): δ = 15.7, 17.5, 20.6 (CH3), 52.6 (OCH3), 126.2 (ArCH), 127.2 (C), 128.8 (2C ArCH), 129.5 (2C ArCH), 133.3 (ArCH), 133.7 136.0, 136.07, 137.2, 138.7, 169.7 (C). IR (neat): ν̃ = 3382 (w), 2940 (s), 1712 (m), 1609 (m), 1530 (m), 1481 (m), 1311 (m), 1213 (m), 1162 (m), 1010 (m), 758 (w) 730 (m) cm −1 . GC-MS (EI, 70 eV): m/z (%): 286 (M + , 58), 253 (100), 240 (8), 211 (15), 178 (6). HRMS (EI): calcd for C17H18O2S [M + ] 286.10220, found 286.10225. 43
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: Mass Spectroscopy: AMD MS40, AMD 40
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 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.
show all

List of used abbreviations - RosDok - Universität Rostock

Create successful ePaper yourself

Delete template?

Save as template?