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For recent examples of synthesis and optical resolution of planar-chiral paracyclophanes, see: (a) Kanomata, N.; Yamada, S.; Ohhama, T.; Fusano, A.; Ochiai, Y.; Oikawa, J.; Yamaguchi, M.; Sudo, F. Tetrahedron 2006, 62, 4128.
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8-BINAP-catalyzed [2 + 2 + 2] cycloadditions, see: (a) Tanaka, K.; Shirasaka, K. Org. Lett. 2003, 5, 4697.
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8-BINAP-catalyzed [2 + 2 + 2] cycloadditions, see: (a) Tanaka, K.; Shirasaka, K. Org. Lett. 2003, 5, 4697.
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(b) Tanaka, K.; Toyoda, K.; Wada, A.; Shirasaka, K.; Hirano, M. Chem. - Eur. J. 2005, 11, 1145.
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(c) Tanaka, K.; Sagae, H.; Toyoda, K.; Noguchi, K. Eur. J. Org. Chem. 2006, 3575.
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For syntheses of cyclophanes via transition-metal-catalyzed or mediated macrocyclization, see: Cobalt-catalyzed [2 + 2 + 2] cycloaddition: (a) Boñaga, L. V. R.; Zhang, H.-C.; Moretto, A. F.; Ye, H.; Gautheir, D. A.; Li, J.; Leo, G. C.; Maryanoff, B. E. J. Am. Chem. Soc. 2005, 127, 3473.
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For syntheses of cyclophanes via transition-metal-catalyzed or mediated macrocyclization, see: Cobalt-catalyzed [2 + 2 + 2] cycloaddition: (a) Boñaga, L. V. R.; Zhang, H.-C.; Moretto, A. F.; Ye, H.; Gautheir, D. A.; Li, J.; Leo, G. C.; Maryanoff, B. E. J. Am. Chem. Soc. 2005, 127, 3473.
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(c) Bonaga, L. V. R.; Zhang, H.-C.; Gautheir, D. A.; Reddy, I.; Maryanoff, B. E. Org. Lett. 2003, 5, 4537.
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Zhang, H.-C.2
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Reddy, I.4
Maryanoff, B.E.5
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(d) Moretto, A. F.; Zhang, H.-C.; Maryanoff, B. E. J. Am. Chem. Soc. 2001, 123, 3157.
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J. Am. Chem. Soc
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Moretto, A.F.1
Zhang, H.-C.2
Maryanoff, B.E.3
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3-catalyzed [2 + 2 + 2] cycloaddition: (e) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784.
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3-catalyzed [2 + 2 + 2] cycloaddition: (e) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784.
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Palladium-catalyzed coupling of enynes: (f) Weibel, D.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1998, 63, 1217.
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Palladium-catalyzed coupling of enynes: (f) Weibel, D.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1998, 63, 1217.
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(g) Saito, S.; Tsuboya, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 5042.
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Cycloaddition of Fischer chromium carbenes with alkynes: (h) Wang, H.; Wulff, D. W.; Rheingold, L. A. J. Am. Chem. Soc. 2003, 125, 8980.
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Cycloaddition of Fischer chromium carbenes with alkynes: (h) Wang, H.; Wulff, D. W.; Rheingold, L. A. J. Am. Chem. Soc. 2003, 125, 8980.
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(i) Wang, H.; Wulff, D. W.; Rheingold, L. A. J. Am. Chem. Soc. 2000, 122, 9862.
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Intramolecular addition of rhodium carbenes: (k) Doyle, M. P.; Hu, W. Synlett 2001, 1364.
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Intramolecular addition of rhodium carbenes: (k) Doyle, M. P.; Hu, W. Synlett 2001, 1364.
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(l) Doyle, M. P.; Hu, W.; Chapman, B.; Marnett, A. B.; Peterson, C. S.; Viatale, P. J.; Stanley, S. A. J. Am. Chem. Soc. 2000, 122, 5718.
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Stanley, S.A.7
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Heck reaction: (m) Dyker, G.; Kadzimirsz, D.; Henkel, G. Tetrahedron Lett. 2003, 44, 7905.
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Heck reaction: (m) Dyker, G.; Kadzimirsz, D.; Henkel, G. Tetrahedron Lett. 2003, 44, 7905.
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For selected examples, see: a
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For selected examples, see: (a) Grimme, S.; Pischel, F.; Vögtle, F.; Nieger, M. J. Am. Chem. Soc. 1995, 117, 157.
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J. Am. Chem. Soc
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(b) Chiu, J.-J.; Hart, H.; Ward, D. L. J. Org. Chem. 1993, 58, 964.
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(c) Takeshita, M.; Tsuzuki, H.; Tashiro, M. Bull. Chem. Soc. Jpn. 1992, 65, 2076.
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See also ref 3e
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(e) See also ref 3e.
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For synthesis of dithiaparacyclophanes by transacetalization, see: a
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For synthesis of dithiaparacyclophanes by transacetalization, see: (a) Ellis-Holder, K. K.; Peppers, B. P.; Kovalevsky, A. Y.; Diver, S. T. Org. Lett. 2006, 8, 2511.
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Org. Lett
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(b) Ellis, K. K.; Wilke, B.; Zhang, Y.; Diver, S. T. Org. Lett. 2000, 2, 3785.
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Org. Lett
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For rhodium-catalyzed reductive coupling of disulfides with alkyl halides using hydrogen as a reducing agent, see: (b) Ajiki, K, Hirano, M, Tanaka, K. Org. Lett. 2005, 7, 4193
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For rhodium-catalyzed reductive coupling of disulfides with alkyl halides using hydrogen as a reducing agent, see: (b) Ajiki, K.; Hirano, M.; Tanaka, K. Org. Lett. 2005, 7, 4193.
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39
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0000320983
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For pioneering work on a metal-catalyzed coupling reaction of thiols and alkyl iodides using a platinum complex as a catalyst, see: (a) Page, P. C. B, Klair, S. S, Brown, M. P, Harding, M. M, Smith, C. S, Maginn, S. J, Mulley, S. Tetrahedron Lett. 1988, 29, 4477
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For pioneering work on a metal-catalyzed coupling reaction of thiols and alkyl iodides using a platinum complex as a catalyst, see: (a) Page, P. C. B.; Klair, S. S.; Brown, M. P.; Harding, M. M.; Smith, C. S.; Maginn, S. J.; Mulley, S. Tetrahedron Lett. 1988, 29, 4477.
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(b) Page, P. C. B.; Klair, S. S.; Brown, M. P.; Smith. C. S.; Maginn, S. J.; Mulley, S. Tetrahedron 1992, 48, 5933.
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Smith, C.S.4
Maginn, S.J.5
Mulley, S.6
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41
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36349036683
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Increasing the reaction temperature decreased the yields of dithiaparacyclophanes
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Increasing the reaction temperature decreased the yields of dithiaparacyclophanes.
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42
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36348985083
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Synthesis and chiroptical properties of planar-chiral dithia[n]cyclophanes were reported. For dithia[n]paracyclophanes. see ref 3e. For dithia[n]metacyclophanes, see ref 8a
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Synthesis and chiroptical properties of planar-chiral dithia[n]cyclophanes were reported. For dithia[n]paracyclophanes. see ref 3e. For dithia[n]metacyclophanes, see ref 8a.
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43
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36349029802
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MOP: 2-(diphenylphosphino)-2′-methoxy-1,1′-binaphthyl. Chiraphos: 2,3-bis(diphenylphosphino)butane. DIOP: 4,5- bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane. i-Pr-Duphos: 1,2-bis(2,5-di-i-propylphospholano)benzene.
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MOP: 2-(diphenylphosphino)-2′-methoxy-1,1′-binaphthyl. Chiraphos: 2,3-bis(diphenylphosphino)butane. DIOP: 4,5- bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane. i-Pr-Duphos: 1,2-bis(2,5-di-i-propylphospholano)benzene.
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44
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36349001835
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In the reactions of dithiols and dibromides shown in Tables 1 and 2 and Schemes 1 and 2, the starting materials were not recovered and insoluble oligomers were obtained as byproducts
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In the reactions of dithiols and dibromides shown in Tables 1 and 2 and Schemes 1 and 2, the starting materials were not recovered and insoluble oligomers were obtained as byproducts.
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45
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0141743671
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For synthesis of fluorenedithia[3.3]paracyclophane copolymers, see: Wang, W.; Xu, J.; Lai, Y.-H. Org. Lett. 2003, 5, 2765.
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For synthesis of fluorenedithia[3.3]paracyclophane copolymers, see: Wang, W.; Xu, J.; Lai, Y.-H. Org. Lett. 2003, 5, 2765.
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