11. (a) Davis, R. A.; Sandoval, I. T.; Concepcion, G. P.; Moreira da Rocha, R.; Ireland, C. M. Tetrahedron 2003, 59, 2855. (b) Liu, H.; Fujiwara, T.; Nishikawa, T.; Mishima, Y.; Nagai, H.; Shida, T.; Tachibana, K.; Kobayashi, H.; Mangindaan, R. E. P.; Namikoshi, M. Tetrahedron 2005, 61, 8611. 12. Kaplan, M. L.; Reents, W. D. Tetrahedron Lett. 1982, 23, 373. 13. Hosoya, Y.; Adachi, H.; Nakamura, H.; Nishimura, Y.; Naganawa, H. Tetrahedron Lett. 1996, 37, 9227. 14. See for example: (a) Dougherty, G.; Hammond, P. D. J. Am. Chem. Soc. 1935, 57, 117. (b) Glass, H. B.; Reid, E. E. J. Am. Chem. Soc. 1929, 51, 3428. For the trifluoromethanesulfonic acid-catalyzed sulfurization <strong>of</strong> cycloalkanes, see: (c) Olah, G. A.; Wang, Q.; Prakash, G. K. S. J. Am. Chem. Soc. 1990, 112, 3697. 15. See for example: Kemp, D. S.; Carey, R. I.; Dewan, J. C.; Galakatos, N. G.; Kerkman, D.; Leung, S.-L. J. Org. Chem. 1989, 54, 1589. 16. See for example: Chua, M.; Hoyer, H. Z. Naturforsch. B 1965, 20, 416. 17. (a) Campbell, J. R. J. Org. Chem. 1964, 29, 1830. (b) Baxter, I.; Ben-Haida, A.; Colquhoun, H. M.; Hodge, P.; Kohnke, F. H.; Williams, D. J. Chem. Eur. J. 2000, 6, 4285. 18. (a) Hilt, G.; Lüers, S. Synthesis 2003, 1784. (b) Hilt, G.; Lüers, S.; Harms, K. J. Org. Chem. 2004, 69, 624. 19. (a) Rashid, M. A.; Reinke, H.; Langer, P. Tetrahedron Lett. 2007, 48, 2321. (b) Rashid, M. A.; Rasool, N.; Adeel, M.; Reinke, H.; Fischer, C.; Langer, P. Tetrahedron 2008, 64, 3782. 92
20. For a review <strong>of</strong> [3+3] cyclizations, see: Feist, H.; Langer, P. Synthesis 2007, 327. 21. For a review <strong>of</strong> 1,3-bis(silyloxy)-1,3-butadienes, see: Langer, P. Synthesis 2002, 441. 22. (a) Chan, T. H.; Brownbridge, P. J. Am. Chem. Soc. 1980, 102, 3534. (b) Brownbridge, P.; Chan, T. H.; Brook, M. A.; Kang, G. J. Can. J. Chem. 1983, 61, 688. 23. (a) Chan, T. H.; Prasad, C. V. C. J. Org. Chem. 1986, 51, 3012. (b) Chan, T. H.; Prasad, C. V. C. J. Org. Chem. 1987, 52, 110. 24. Imran, M.; Iqbal, I.; Rasool, N.; Rashid, M. A.; Langer, P. Synlett 2008, 2708. 25. Iqbal, I.; Imran, M.; Villinger, A.; Langer, P. Synthesis 2009, 297. 26. Rashid, M. A.; Rasool, N.; Iqbal, I.; Imran, M.; Langer, P. Tetrahedron Lett. 2008, 49, 2466. 27. Danishefsky, S. J. Acc. Chem. Res. 1979, 66. 28. For a spiro-activation, see for example: Zefirov, N. S.; Kozhushkov, S. I.; Kuznetsova, T. S. Tetrahedron 1982, 38, 1693. 29. Appel, B.; Rotzoll, S.; Reinke, H.; Langer, P. Eur. J. Org. Chem. 2006, 3638. 30. CCDC-700707 contains all crystallographic details <strong>of</strong> this publication and is available free <strong>of</strong> charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; Fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk. 93
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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
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Table 5. Synthesis of arenes 14a-l
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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 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: Refrences 1. Handbook of Chemistry
- 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.