Substitution of a haloquinone by phenols under pyridine-free conditions: Synthetic, mechanistic, and solid-state considerations involving 2,3-dichloro- 1,4-naphthoquinone

Nolan J. Blythe, Kristin M. Hutchins, Joshua R. Carpenter, Taylor W. Cox, Andrew M. Johnson, Leonard R. MacGillvray, Jay W. Wackerly

Research output: Contribution to journalArticle

1 Scopus citations

Abstract

Benzoquinones fused to heterocycles, like most benzoquinones, have the potential for a wide-array of applications but their inherent reactivity can present a synthetic dilemma. The issue is that a synthesis may target one desired outcome, yet yield a range of side products. In efforts to understand the reaction pathways of haloquinone substitution, while minimizing undesired product formation, four examples of reactions between 2,3-dichloro-1,4-naphthoquinone and phenolic nucleophiles are presented. Two of the products were confirmed and analyzed by X-ray crystallography. The reaction with orcinol was optimized for yield and investigation of this mechanism indicates a novel pathway under pyridine-free conditions.

Original languageEnglish
Pages (from-to)379-386
Number of pages8
JournalHeterocycles
Volume98
Issue number3
DOIs
StatePublished - 2019

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