title: Synthesis of 3,5- and 3,6-linked calix[n]naphthalenes.
abstract: The preparation of calix[n]naphthalenes from derivatives of 2,7-dihydroxynaphthalene is described. 1,8-Dialkyl substitution is used to direct the regiochemistry of the acid-catalyzed condensation reactions. Acyclic peri substituents lead to a 3,5-linked calix[3]naphthalene, whereas cyclic peri substituents give predominantly a calix[5]naphthalene with the corresponding 3,6-linkage. The 3,6-linked calix[4]naphthalene is prepared in pure form by a dimerization strategy.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
authors.forename: Berkeley J
authors.initials: BJ
authors.lastname: Shorthill
authors.forename: Robert G
authors.initials: RG
authors.lastname: Granucci
authors.forename: Douglas R
authors.initials: DR
authors.lastname: Powell
authors.forename: Timothy E
authors.initials: TE
authors.lastname: Glass
mesh_terms: D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009281:Naphthalenes