1. Synthesis and some transformations of polybrominated quinone diazides.
- Author
-
Vasin, V., Fadin, M., and Tarasova, I.
- Subjects
- *
NITROPHENOLS , *AQUEOUS solutions , *SULFURIC acid , *RING formation (Chemistry) , *ACETONITRILE - Abstract
The reduction of polybrominated o- and p-nitrophenols with granular tin in concentrated aqueous HCl gave polybrominated aminophenols which were diazotized with sodium nitrite in concentrated sulfuric acid at 0°C to obtain polybrominated o- and p-quinone diazides. Their thermolysis with elimination of nitrogen generated ketocarbenes which reacted with acetylacetone to form insertion products at the activated methylene group. Ketocarbenes generated from o-quinone diazides reacted with typical dipolarophiles such as acetonitrile, benzonitrile, styrene, and phenylacetylene to afford the corresponding [3 + 2]-cycloaddition products. [ABSTRACT FROM AUTHOR]
- Published
- 2017
- Full Text
- View/download PDF