Synthesis of 3,5- and 3,6-linked calix[n]naphthalenes

Berkeley J Shorthill; Robert G Granucci; Douglas R Powell; Timothy E Glass

doi:10.1021/jo0161173

Synthesis of 3,5- and 3,6-linked calix[n]naphthalenes

J Org Chem. 2002 Feb 8;67(3):904-9. doi: 10.1021/jo0161173.

Authors

Berkeley J Shorthill¹, Robert G Granucci, Douglas R Powell, Timothy E Glass

Affiliation

¹ Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.

PMID: 11856035
DOI: 10.1021/jo0161173

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Dimerization
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Conformation
Molecular Structure
Naphthalenes / chemical synthesis*
Naphthalenes / chemistry

Substances

Naphthalenes

Abstract

Publication types

MeSH terms

Substances

Grants and funding