5273-62-1

Upstream product

• 14624-11-4 cis-4.5-dichloro-cyclohexene-⁽¹⁾-dione-(3.6) 
• 106-51-4 p-benzoquinone 
• 123-31-9 hydroquinone 

Downstream Products

• 57982-12-4 2,3-dichlorohydroquinone diacetate 
• 71155-99-2 2,5-dichlorohydroquinone diacetate 
• 608-44-6 2,3-dichlorohydroquinone 
• 123-31-9 hydroquinone 
• 57165-98-7 2,5,6-trichloro-cyclohex-2-ene-1,4-dione 
• 57166-01-5 Methyl-6-chlorhomogentisat 
• 824-69-1 2,5-dichloro-1,4-hydroquinone 
• 39542-65-9 2,3-dichloro-4-methoxyphenol 
• 39542-69-3 2,5-Dimethoxy-3,4-dichlor-allylbenzol 
• 39542-67-1 1-Allyloxy-2,3-dichlor-4-methoxybenzol 
• 39542-68-2 2,3-Dichlor-4-methoxy-6-allylphenol 
• 39542-66-0 2,3-dichlorohydroquinone dimethyl ether 
• 608-94-6 2,3,5-trichloro-1,4-hydroquinone 
• 615-67-8 chloro-p-hydroquinone 

Relevant academic research and scientific papers

ELECTROCHEMICAL BEHAVIOUR OF SUBSTITUTED HYDROQUINONES

The oxidation potentials of thirteen hydroquinones substituted by chlorine, pyrazol-1-yl and 3,5-dimethylpyrazol-1-yl groups were experimentally determined by cyclic voltammetry.The estimated half-wave potentials E1/2 have been discussed taking into account the inductive and conjugative substituent effects.Key words: Cyclic voltammetry, Hydroquinones, Redox, Pyrazoles

Benzoquinones and Related Compounds. Part 4. Thermolysis of the Diels-Alder Adduct of 2-Acetyl-5,6-dichloro-1,4-benzoquinone and Cyclopentadiene: Evidence for a Partial Retro-diene Reaction

Addition of chlorine to (2-methyl-1,3-dioxolan-2-yl)-1,4-benzoquinone occurs at the unsubstituted double bond.Subsequent enolisation and cleavage of the acetal affords 2-acetyl-5,6-dichlorohydroquinone in 50percent overall yield.Oxidation of this gives the corresponding 1,4-benzoquinone which with cyclopentadiene yields, predominantly, the 1 : 1 Diels-Alder adduct (6) by endo-addition to the 2,3-double bond.Thermolysis of this adduct in benzene results in disproportionation to cyclopentadiene and the spiro-acetal (13); thermolysis in acetic acid also yields (13), but the major product is the dihydrobenzofuran (14), an isomer of the Diels-Alder adduct.Mechanisms for the formation of these products are discussed.