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Relevant academic research and scientific papers

Tetranitromethane as an efficient reagent for the conversion of epoxides into β-hydroxy nitrates

A convenient regioselective method for the preparation of β-hydroxy nitrates based on the ring opening reaction of epoxides by tetranitromethane in the presence of triethylamine is described. A series of substituted β-hydroxy nitrates were obtained in high yields under mild conditions.

Efficient regio- and stereoselective conversions of oxiranes and aziridines into β-(nitrooxy)-substituted alcohols and amines by using bismuth nitrate

Oxiranes and aziridines efficiently undergo ring opening with bismuth nitrate at room temperature to furnish the corresponding β-(nitrooxy)- substituted alcohols and amines respectively. The conversions are highly regio- and stereoselective and afford the

Zirconyl nitrate mediated regioselective ring opening of epoxides and aziridines: an easy synthesis of β-nitrato-alcohols and -sulfonamides

Epoxides and aziridines are cleaved efficiently and regioselectively in the presence of zirconyl nitrate at room temperature to afford the corresponding β-nitrato-alcohols and -sulfonamides, respectively, in high yields.

Determination of the hydroxy nitrate yields from the reaction of C2-C6 alkenes with OH in the presence of NO

The yields of hydroxy nitrates from the reaction of selected C2-C6 alkenes with OH in the presence of NO were measured at 296 ± 3 K in a 9600 L photochemical smog chamber. Hydroxyl radicals were produced from the photolysis of isopropyl nitrite in the presence of NO. The loss of the alkene was followed using gas chromatography. The hydroxy nitrate products were determined using a combination of capillary chromatography and an organic nitrate specific chemiluminescence detector. The yield of hydroxy nitrates was observed to increase with the size of the precursor alkene as follows: ethene (0.86%), propene (1.5%), 1-butene (25%), cis-2-butene (3.4%), and 1-hexene (5.5%). Previous studies involving the production of alkyl nitrates from alkanes show a similar trend, but the yields reported here are a factor of 2-3 lower than for the corresponding simple alkylperoxy radical. The impact of a β-hydroxy group on the nitrate yield is examined using an ab initio molecular orbital study. It indicates that a hydrogen-bonded peroxy nitrite intermediate is formed, which results in a decrease in D0(O-O) for the peroxy linkage of about 8 kJ/mol. This would be expected to effectively decrease the organic nitrate yield. The implications of these findings for the organic nitrate path as an atmospheric NOx removal mechanism are discussed.

Ceric ammonium nitrate: A mild and efficient reagent for conversion of epoxides to β-nitrato alcohols

Catalytic amount of Ce(IV) as ceric ammonium nitrate (CAN) alone or in the presence of excess nitrate ion reacts smoothly and efficiently with epoxides under mild conditions to produce the corresponding β-nitrato alcohols in good to excellent yields.

Synthesis and antihypertensive activities of new 1,4-dihydropyridine derivatives containing nitrooxyalkylester moieties at the 3- and 5-positions

We have synthesized new 1,4-dihydropyridine derivatives having nitrooxyalkylester moieties at the 3- and 5-positions in order to develop potent and long-lasting vasodilators. The antihypertensive activities of these compounds were compared with that of nifedipine. One of them, 2- nitrooxypropyl 3-nitrooxypropyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydro- 3,5-pyridinedicarboxylate (CD-349) was selected for further development. The structure-activity relationship is discussed.