Synthesis and characterization of 2,7-di(tert-butyl)pyreno[4,5-c:9,10-c']difuran and derived pyrenophanes.
Isobenzofurans (IBF)s have seen widespread use in the synthesis of both natural products and polycyclic aromatic hydrocarbons. There are few examples that have two IBF entities linked in a fused aromatic ring system. Here we present the synthesis and characterization of a bis(IBF), 2,7-di(tert-butyl)pyreno[4,5-c:9,10-c']difuran. Reaction with bis(maleimide) dienophiles gives pyrenophanes. The solid-state structures of the bis(IBF) and two cyclophanes are discussed.
Franz
David
D
Department of Chemistry and Biochemistry, University of Lethbridge, 4401 University Drive, Lethbridge, Alberta T1K 3M4, Canada.
Robbins
Steven J
SJ
Boeré
René T
RT
Dibble
Peter W
PW
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry*; D002073:Butanes / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
C545419:2,7-di(tert-butyl)pyreno(4,5-c-9,10-c')difuran; D001572:Benzofurans; D002073:Butanes; D005663:Furans; D011083:Polycyclic Compounds; C545420:pyrenophane