Synthesis of 3,5- and 3,6-linked calix[n]naphthalenes.
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.
Shorthill
Berkeley J
BJ
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Granucci
Robert G
RG
Powell
Douglas R
DR
Glass
Timothy E
TE
D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
D009281:Naphthalenes