Epoxidation of Bicyclo[2.2.1]hept-5-ene-2,3-endo- and Exodicarboxylic Acid N-Arylimides

Epoxidation of endo- and exo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid N-arylimides with a solution of peracetic acid in anhydrous dioxane affords 5,6-exo-epoxybicycloheptanedicarboxylic acid N-arylimides. The epoxidation reaction is not sensitive to the configuration of the imide fragment, to the character and position of the substituent in the aromatic ring. The reaction is determined only by oxidation conditions.     

Oxidative bromination of aniline and its derivatives

Oxidative bromination of aniline and its derivatives containing various substituents (CH₃, Cl, NO₂, COOH) in ortho, meta, and para positions with a brominating mixture of NaBr (KBr) and 20–22% hydrogen peroxide in 6–8% hydrochloric acid at the molar ratio aniline : NaBr (KBr) : H₂O₂ : HCl = 1 : 3.5 : 3.2 : 4.5 is described.     

Synthesis of <Emphasis Type="Italic">endo,exo</Emphasis>-1,2,3,4,11,11-hexachlorotricyclo[6.2.1.05,10]-undec-2-en-7,8-dicarboxylic acid <Emphasis Type="Italic">N</Emphasis>-(2,4,6-tribromophenyl)imide

Apreparation method was developed for endo,exo-1,2,3,4,11,11-hexachlorotricyclo-[6.2.1.0^5,10]undec-2-ene-7,8-dicarboxylic acid N-tribromophenylimide by acylation of 2,4,6-tribromoaniline with this acid anhydride. The structure of imide obtained was proved by IR spectrum, TLC method, and by independent synthesis.