Synthesis of Functional Derivatives of Benzodifurazan{Benzo[1,2-c:3,4-c’]bis([1,2,5]oxadiazole)}

We have found that BDP reacts with 1,3-dibromo-5,5-dimethylhydantoin in sulfuric acid to form 5-bromo-4,5-dihydrobenzo[1,2-c:3,4-c']bis([1, 2,5]oxadiazol)-4-ol, which upon treatment with a base(calcium hydroxide) turns into 1a,7b-dihydrooxireno[2',3':5,6]benzo[1,2-c:3,4-c']bis([1,2,5]oxadiazole). The structure of the compound was established by X-ray diffraction. The resulting compound exhibits the usual properties of epoxides. Easily adds nucleophiles to form the corresponding alcohols, which, when treated with p-toluenesulfonyl chloride in the presence of tetrabutylammonium bromide and sodium hydroxide in benzene, give functional derivatives of BDF.

benzodifurazan, oxiranes(epoxides), phase transfer catalysis, 1,3-dibromo-5,5-dimethylhydantoin