Abstract
Dimer 9, which is representative of diaryl methane structures reported present in residual lignin, was reacted with aqueous chorine at 50 o C. The major product was identified as the tetrachloroquinone dimer 13 (x=2, y= 2). Similar reaction of the tetrachorocatechol dimer 12 with aqueous chorine gave a mixture of the tetrachloroquinones 15 and 16. When the mixture of the quinones was reacted with 2.5% sodium hydroxide, an intramolecular oxidation-reduction (Cannizzaro) reaction with the simultaneous loss of two chlorine atoms occurred as the main reaction. The products, 21, were characterized as having a chlorine-free muconic acid lactone group attached to a dichlorocatechol
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