Research in Energetic Compounds
Interim summary rept. 1 Jan-31 Dec 1983
FLUOROCHEM INC AZUSA CA
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The synthesis of 1,3,3-trinitroazetidine was carried out by means of the reaction of 1-t-butyl-3-methanesulfonatoazetidine with sodium nitrite to give 1-t-butyl-3-nitroazetidine. Oxidative nitration gave 1-t-butyl-3,3- dinitroazetidine, and nitrolysis with acetyl nitrate gave 1,3,3- trinitroazetidine. Other routes were explored. 1-Benzhydryl-3,3-dinitroazetidine was obtained by nitrite displacement of 1-benzhy-dryl-3- methanesulfonatoazetidine, followed by oxidative nitration, but attempts to replace the benzhydryl group by nitrolysis, hydrogenation or bromination were unsuccessful. Nitration of 1-t-butyl-3-hydroxyazetidine, 3- methanesulfonatoazetidine, 3-carboxyazetidine and 3-hydroxyazetidine gave, respectively, 1-t-butyl3-nitratoazetidine, 1-nitro-3-methanesulfonatoazetidine, 3-carboxy-1-nitroazetidine and 1-nitro-3-nitratoazetidine. Bromination of 2,4- dioximinoadamantane under mildly acidic conditions gave 2,4-dibromo-2,4- dinitroadamantane. Reactions of 2-oximino-adamantane, 2,4,-dioximinoadamantane and 2,6-dioximinobicyclo3.3.1-nonane with neutralized hypochlorous acid resulted in replacement of the oxime groups with gem-dichloro groups.
- Organic Chemistry