Issue 3, 2001

Synthesis of cyanodibenzo[1,4]dioxines and their derivatives by cyano-activated fluoro displacement reactions

Abstract

A new group of cyanodibenzo[1,4]dioxines have been synthesized by cyano-activated fluoro displacement reactions between cyanodifluorobenzenes and catechols in DMF at 130 °C in the presence of potassium carbonate. This route is exemplified by the synthesis of cyanodibenzo[1,4]dioxines from several substituted catechols. The reactions are virtually quantitative. Cyanodibenzo[1,4]dioxines were hydrolysed with potassium hydroxide in ethylene glycol or converted into amide derivatives to yield additional substituted dibenzo[1,4]dioxines. Cyanodibenzo[1,4]-dioxines are fluorescent and excitation and emission data are presented. Improved syntheses of 4,5-diphenylveratrole and 3,6-dimethylcatechol, the latter involving reduction of a phenolic Mannich base at atmospheric pressure, have been elaborated.

Supplementary files

Article information

Article type
Paper
Submitted
19 Oct 2000
Accepted
23 Dec 2000
First published
21 Feb 2001

New J. Chem., 2001,25, 379-384

Synthesis of cyanodibenzo[1,4]dioxines and their derivatives by cyano-activated fluoro displacement reactions

G. C. Eastmond, J. Paprotny, A. Steiner and L. Swanson, New J. Chem., 2001, 25, 379 DOI: 10.1039/B008508L

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