Synlett 2016; 27(14): 2113-2116
DOI: 10.1055/s-0035-1562726
cluster
© Georg Thieme Verlag Stuttgart · New York

Kinetic Stabilization of a Highly Bent Pyrene System

Baozhong Zhang
Department of Chemistry, Memorial University of Newfoundland, St. John’s, NL, A1B 3X7, Canada   Email: gbodwell@mun.ca
,
Yuming Zhao
Department of Chemistry, Memorial University of Newfoundland, St. John’s, NL, A1B 3X7, Canada   Email: gbodwell@mun.ca
,
Graham J. Bodwell*
Department of Chemistry, Memorial University of Newfoundland, St. John’s, NL, A1B 3X7, Canada   Email: gbodwell@mun.ca
› Author Affiliations
Further Information

Publication History

Received: 07 July 2016

Accepted after revision: 13 July 2016

Publication Date:
18 July 2016 (online)

Abstract

With the aim of accessing a new record holder for the most bent pyrene system, a new type of pyrenophane was designed that incorporates both a means for tuning the degree of bend in the pyrene system and buttressing phenyl groups for kinetic stabilization. The synthesis of the first member of this class of compounds is described.

Supporting Information

 
  • References

  • 2 Brown CJ, Farthing AC. Nature (London, U.K.) 1949; 164: 915
  • 3 Tsuji T, Okuyama M, Ohkita M, Kawai H, Suzuki T. J. Am. Chem. Soc. 2003; 125: 951
  • 4 Mitra NK, Meudom R, Corzo HH, Gorden JD, Merner BL. J. Am. Chem. Soc. 2016; 138: 3235
  • 6 Mitchell RH, Boekelheide V. J. Am. Chem. Soc. 1970; 92: 3510
  • 7 Bodwell GJ, Fleming JJ, Miller DO. Tetrahedron 2001; 57: 3577
  • 8 Bodwell GJ, Bridson JN, Houghton TJ, Kennedy JW. J, Mannion MR. Chem. Eur. J. 1999; 5: 1823
  • 9 Bodwell GJ, Bridson JN, Cyrański M, Kennedy JW. J, Krygowski M, Mannion MR, Miller DO. J. Org. Chem. 2003; 68: 2089
  • 10 Bodwell GJ, Fleming JJ, Mannion MR, Miller DO. J. Org. Chem. 2000; 65: 5360
  • 11 Zhang B, Manning GP, Dobrowolski MA, Cyrański MK, Bodwell GJ. Org. Lett. 2008; 10: 273
  • 12 Bodwell GJ, Houghton TJ, Koury HE, Yarlagadda B. Synlett 1995; 751
  • 13 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr. JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision E.01. Gaussian, Inc; Wallingford CT: 2009
  • 14 Bodwell GJ, Bridson JN, Houghton TJ, Kennedy JW. J, Mannion MR. Angew. Chem., Int. Ed. Engl. 1996; 35: 1320 ; Angew. Chem. 1996, 108, 1418