Pyrolysis of p-Benzosemiquinone

Autor: Richard C. Reiter, Lance J. Heinle, Cheryl D. Stevenson
Rok vydání: 2001
Předmět:
Zdroj: The Journal of Organic Chemistry. 67:119-124
ISSN: 1520-6904
0022-3263
DOI: 10.1021/jo010646p
Popis: 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.
Databáze: OpenAIRE