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DOI: 10.1055/s-0034-1379006
1,4-Naphthoquinone
Publication History
Publication Date:
08 September 2014 (online)
Introduction
1,4-Naphthoquinone (1) is a yellow crystal, slightly soluble in water, soluble in benzene, diethyl ether, chloroform, glacial acetic acid, etc. Having two reactive functional groups, a C–C double bond and two ketone carbonyls, 1,4-naphthoquinone has been widely applied in organic reactions, such as Michael-type additions,[1] aldol-type reactions, Diels–Alder reactions,[2] cycloadditions,[3] Friedel–Crafts reactions,[4] and epoxidation.[5] Further, 1,4-naphthoquinones are widely used in antibacterial and antitumor drugs, and it is an important structural motif in many natural products, such as vitamin K. In addition, its derivatives are also used in industry on a ton scale as dye reagents. 1,4-Naphthoquinone is commercially available (CAS number: 130-15-4) and can be prepared industrially by the oxidation of naphthalene using vanadium pentoxide (V2O5) as catalyst.
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References
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