Synlett, Inhaltsverzeichnis Synlett 2013; 24(19): 2545-2549DOI: 10.1055/s-0033-1339882 letter © Georg Thieme Verlag Stuttgart · New York Towards a Perylene-Containing Nanohoop Joel M. Batson Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA Fax: +1(617)2537929 eMail: tswager@mit.edu , Timothy M. Swager* Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA Fax: +1(617)2537929 eMail: tswager@mit.edu › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract We report the synthesis of a belt-shaped macrocycle, herein referred to as a nanohoop, that contains binaphthyl moieties separated by phenyl groups. Key words Key wordsmacrocycles - arenes - biaryls - Diels–Alder reaction - cyclization Volltext Referenzen References and Notes 1a Tian X, Jasti R. Syntheses of Cycloparaphenylenes: The Shortest-Possible Segments of Armchair Carbon Nanotubes, In Fragments of Fullerenes and Carbon Nanotubes: Designed Synthesis, Unusual Reactions, and Coordination Chemistry. Petrukhina MA, Scott LT. Wiley; Hoboken: 2012 1b Hirst ES, Jasti R. J. Org. Chem. 2012; 77: 10473 1c Evans PJ, Jasti R. Top. Curr. Chem. 2013; DOI: 10.1007/128_2012_415 2 Jasti R, Bhattacharjee J, Neaton JB, Bertozzi CR. J. Am. Chem. Soc. 2008; 130: 17646 3a Segawa Y, Miyamoto S, Omachi H, Matsuura S, Senel P, Sasamori T, Tokitoh N, Itami K. Angew. Chem. Int. Ed. 2011; 50: 3244 3b Sisto TJ, Golder MR, Hirst ES, Jasti R. J. Am. Chem. Soc. 2011; 133: 15800 3c Yamago S, Watanabe Y, Iwamoto T. Angew. Chem. Int. Ed. 2010; 49: 757 3d Takaba H, Omachi H, Yamamoto Y, Bouffard J, Itami K. Angew. Chem. Int. Ed. 2009; 48: 6112 3e Kayahara E, Sakamoto Y, Suzuki T, Yamago S. Org. Lett. 2012; 14: 3284 3f Segawa Y, Senel P, Matsuura S, Omachi H, Itami K. Chem. Lett. 2011; 40: 423 3g Omachi H, Segawa Y, Itami K. Org. Lett. 2011; 13: 2480 3h Iwamoto T, Watanabe Y, Sakamoto Y, Suzuki T, Yamago S. J. Am. Chem. Soc. 2011; 133: 8354 4a Xia J, Jasti R. Angew. Chem. Int. Ed. 2012; 51: 2474 4b Kayahara E, Iwamoto T, Suzuki T, Yamago S. Chem. Lett. 2013; 42: 621 5 Bachrach SM, Stück D. J. Org. Chem. 2010; 75: 6595 6a Steinber BD, Scott LT. Angew. Chem. Int. Ed. 2009; 48: 5400 6b Omachi H, Nakayama T, Takahashi E, Segawa Y, Itami K. Nature Chem. 2013; 5: 572 7 Fort EH, Donovan PM, Scott LT. J. Am. Chem. Soc. 2009; 131: 16006 8 Yagi A, Segawa Y, Itami K. J. Am. Chem. Soc. 2012; 134: 2962 9a Minkin VI, Glukhovtsev MN, Simkin BY. Aromaticity and Antiaromaticity. Electronic and Structural Aspects. J. Wiley & Sons; New York: 1994 9b Garratt PK. Aromaticity. Wiley; New York: 1986 10a Ajaz A, McLaughlin EC, Skraba SL, Thamatam R, Johnson RP. J. Org. Chem. 2012; 77: 9487 10b Dou X, Yang X, Bodwell GJ, Wagner M, Enkelmann V, Müllen K. Org. Lett. 2007; 9: 2485 11 For a discussion on the synthesis and properties of poly(para-phenylene) and its derivatives, see: Grimsdale AC, Mullen K. Adv. Polym. Sci. 2006; 199: 1 ; and references cited therein 12 A 7 mL microwave vial containing a magnetic stirring bar was flame-dried under vacuum and back-filled with argon after cooling to room temperature. To this vial was added 4 (18.2 mg, 10 μmol), TsOH·H2O (30.4 mg, 0.16 mmol), and anhydrous toluene (3.00 mL). The vial was then sealed and heated in a CEM Discover Microwave, stirring at 150 °C for 60 min. After the reaction mixture was cooled to room temperature, dichloromethane was added and the organic layer was washed with 1 M aq NaOH (× 3). The organic and aqueous layers were then separated prior to washing the organic layer with brine. The cumulative organic layer was dried with sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was subjected to column chromatography (CH2Cl2–hexane, 20:80) to afford 1 (4.9 mg, 38%) as an off-white, slightly yellow solid. 1H NMR (500 MHz, DMSO-d6, 150 °C): δ = 8.13 (1 H), 8.02 (2 H), 7.77 (1 H), 7.71 (3 H), 7.56 (5 H), 7.43 (2 H). MADLI-TOF MS: m/z calcd for C102H70: 1306.55; found: 1306.84. 13a Fujitsuka M, Cho DW, Iwamoto T, Yamago S, Majima T. Phys. Chem. Chem. Phys. 2012; 14: 14585 13b Segawa Y, Fukazawa A, Matsuura S, Omachi H, Yamaguchi S, Irle S, Itami K. Org. Biomol. Chem. 2012; 10: 5979 Zusatzmaterial Zusatzmaterial Supporting Information