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Communication | Regular issue | Vol 98, No. 3, 2019, pp.379-386
Published online, 7th March, 2019
DOI: 10.3987/COM-19-14035
■ 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, and Jay Wm. Wackerly*

*Department of Chemistry, Central College, Pella, IA 50129, U.S.A.

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.