Pyrolysis of p-benzosemiquinone.
In contrast to the thermolysis of p-benzoquinone, which does not decompose until the temperature is over 800 degrees C, and then primarily yields vinylacetylene, the corresponding anion radical, precipitated from liquid ammonia [Na(+)(NH(3))C(6)H(4)O(2)(*-)], decomposes at 380 degrees C and fragments primarily into phenol, hydroquinone, ammonia, methane, carbon monoxide, hydrogen, and minor amounts of other simple compounds. When the benzoquinone is replaced with perdeuteriobenzoquinone, deuterium and hydrogen are randomly scrambled into the products, and both ND(3) and CH(4) are formed. When the hot pyrolysis container is completely sealed, preventing the escape of volatile materials, p-aminophenol, as opposed to phenol, is the major liquid product.
Stevenson
Cheryl D
CD
Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, USA. stevenson@xenon.che.ilstu.edu
Heinle
Lance J
LJ
Reiter
Richard C
RC
D000627:Aminophenols / Q000138:chemical synthesis; D000641:Ammonia / Q000737:chemistry; D016227:Benzoquinones / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006358:Hot Temperature; D019110:Meteoroids; D013696:Temperature
D000627:Aminophenols; D016227:Benzoquinones; D005609:Free Radicals; C025232:semiquinone radicals; D000641:Ammonia