Epoxides, ring-opening nitration

Synthesis of vicinal dInItrate esters from the ring opening nitration of epoxides with dinitrogen pentoxide (Ref. 75) ... 

A suspension of thallium (III) nitrate in hexane reacts with epoxides to give the corresponding -hydroxy nitrate esters in good yield. The same reagent in acetonitrile has been used to synthesize a-nitratoketones from substituted acetophenones, 1,2-dinitrate esters from alkenes, and 1,3-dinitrates from ring-opening nitration of cyclopropanes. ... 

Amines can be prepared using reactions including epoxide ring opening, addition of nitrogen nucleophiles to carbonyls followed by reduction, reduction of amides, reduction of nitriles, and nitration of arenes followed by reduction. 

Nichols and co-workersstudied the formation of j8-hydroxy nitrate esters via the acid-catalyzed ring-opening of epoxides with nitrate anion. Reactions were conducted in aqueous media using solutions of ammonium nitrate is nitric acid and under nonaqueous conditions using solutions of pure nitric acid in chloroform. 2-Nitratoethanol (32) is formed in 58 % yield from ethylene oxide (30) using either of these methods. ... 

Azidolysis of glycidic acids. In the presence of copper(II) nitrate trihydrate, regioselective ring opening of the epoxide by sodium azide in water (pH 4) to provide 3-azido-2-hydroxy carboxylic acids is observed. 

Ammonium hexanitratocerate(IV) can be used as a catalyst for the ring opening of epoxides in presence of water, thiols or acetic acid (scheme 21) (Iranpoor et al., 1991). Epoxides react in presence of an excess of nitrate ions and a catalytic amount of ammonium hexanitra-tocerate(IV) in acetonitrile to /3-nitrato alcohols (Iranpoor and Salehi, 1995). A combination of ammonium hexanitratocerate(IV) and A-bromosuccinimide (NBS) transforms epoxides into a-hydroxy ketones (scheme 22) (Surendra et al., 2005). Aziridines give a-aminoketones under the same conditions. 

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