Issue 12, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Chemical reactivity of hydroxymethylnaphthols: hetero-Diels–Alder products of o-naphthoquinomethides derived from 2- and 3-hydroxymethylnaphthols

Muhammad Ashram,a   David O. Millerb  and  Paris E. Georghiou*c  

* Corresponding authors

a Department of Chemistry, Mu'Tah University, Al Karak, Jordan

b X-Ray Crystallography Unit, Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland, Canada,

c Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland, Canada,
E-mail: parisg@mun.ca

Abstract

In relation to the syntheses of exo- and endo-calixnaphthalenes, the chemical reactions of several 2- and 3-hydroxymethylnaphthols, as well as other substituted naphthols, with formaldehyde under a variety of condensation reaction conditions were evaluated. In several instances, o-naphthoquinomethides were the putative intermediates which were formed and which resulted in hetero-Diels–Alder [4+2]cyclodimerization spiro products.

Graphical abstract: Chemical reactivity of hydroxymethylnaphthols: hetero-Diels–Alder products of o-naphthoquinomethides derived from 2- and 3-hydroxymethylnaphthols

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Article information

DOI
https://doi.org/10.1039/B200893A
Article type
Paper
Submitted
23 Jan 2002
Accepted
15 Apr 2002
First published
14 May 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1470-1476

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Chemical reactivity of hydroxymethylnaphthols: hetero-Diels–Alder products of o-naphthoquinomethides derived from 2- and 3-hydroxymethylnaphthols

M. Ashram, D. O. Miller and P. E. Georghiou, J. Chem. Soc., Perkin Trans. 1, 2002, 1470 DOI: 10.1039/B200893A

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