Reactivity of quinones for the dehydrogenation of poly(1,3‐cyclohexadiene)

Abstract The reactivity of three types of quinones (3,4,5,6‐tetrachloro‐1,2‐(o‐)‐benzoquinone (TOQ), 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ), and 2,3,5,6,‐tetrachloro‐1,4‐(p‐)‐benzoquinone (TCQ)) was examined for the dehydrogenation of poly(1,3‐cycohexadiene) (PCHD) composed of 1,2‐cyclohexadiene and 1,4‐cyclohexadiene units. The order of reactivity was TOQ > DDQ > TCQ. The steric hindrance of CO groups in the quinones appeared to be an important factor in determining their reactivity. DDQ was found to be an appropriate dehydrogenation reagent for PCHD. The reactivity of TCQ was considerably low for PCHD containing 1,2‐cyclohexadiene units. The reactivity of TOQ was too high and side reactions occurred, causing the formation of structural defects. Copyright © 2007 Society of Chemical Industry