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Synthesis of 3,5- and 3,6-linked calix[n]naphthalenes
Berkeley J Shorthill1, Robert G Granucci, Douglas R Powell
1Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
The Journal of Organic Chemistry
|February 22, 2002
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.