- Hydroxylamine Reactions with Peroxide Products of Alkenes Ozonolysis
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Reactions were studied of peroxide ozonolysis products obtained from linear and cyclic alkenes with hydroxylamine prepared in situ from NH2OH·HCl by hydrogen chloride neutralization with sodium acetate. A one-pot reactions sequence was performed: alkene oxidation with ozone → reduction to a carbonyl compound with hydroxylamine → condensation of the carbonyl compound with hydroxylamine providing a possibility of direct transformation of alkenes in keto- and aldoximes excluding the stage of preparation and isolation of the carbonyl compound.
- Legostaeva, Yu. V.,Garifullina,Nazarov,Ishmuratova,Ishmuratov, G. Yu.
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p. 1122 - 1126
(2018/10/24)
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- Transformations of peroxide products of olefin ozonolysis in tetrahydrofuran in reactions with hydroxylamine and semicarbazide hydrochlorides
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Treatment with hydroxylamine and semicarbazide hydrochlorides of peroxide products obtained by ozonolysis of olefins in tetrahydrofuran gives mainly carboxylic acids and their derivatives.
- Ishmuratov,Legostaeva,Garifullina,Botsman,Muslukhov,Ishmuratova,Tolstikov
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p. 928 - 933
(2014/10/15)
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- Intermolecular cope-type hydroamination of alkenes and alkynes
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(Chemical Equation Presented) Keep it simple! Intermolecular hydroamination can be achieved simply upon heating alkynes and alkenes with aqueous hydroxylamine. Alkynes react to afford oximes in good to excellent yields, and the formation of Markovnikov products is favored. A mechanism involving Cope-type hydroamination followed by bimolecular proton transfer is suggested and supported by DFT studies.
- Beauchemin, Andre M.,Moran, Joseph,Lebrun, Marie-Eve,Seguin, Catherine,Dimitrijevic, Elena,Zhang, Lili,Gorelsky, Serge I.
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p. 1410 - 1413
(2008/12/23)
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- Intermolecular Cope-type hydroamination of alkenes and alkynes using hydroxylamines
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The development of the Cope-type hydroamination as a method for the metal- and acid-free intermolecular hydroamination of hydroxylamines with alkenes and alkynes is described. Aqueous hydroxylamine reacts efficiently with alkynes in a Markovnikov fashion to give oximes and with strained alkenes to give N-alkylhydroxylamines, while unstrained alkenes are more challenging. N-Alkylhydroxy-lamines also display similar reactivity with strained alkenes and give modest to good yields with vinylarenes. Electron-rich vinylarenes lead to branched products while electron-deficient vinylarenes give linear products. A beneficial additive effect is observed with sodium cyanoborohydride, the extent of which is dependent on the structure of the hydroxylamine. The reaction conditions are found to be compatible with common protecting groups, free OH and NH bonds, as well as bromoarenes. Both experimental and theoretical results suggest the proton transfer step of the N-oxide intermediate is of vital importance in the intermolecular reactions of alkenes. Details are disclosed concerning optimization, reaction scope, limitations, and theoretical analysis by DFT, which includes a detailed molecular orbital description for the concerted hydroamination process and an exhaustive set of calculated potential energy surfaces for the reactions of various alkenes, alkynes, and hydroxylamines.
- Moran, Joseph,Gorelsky, Serge I.,Dimitrijevic, Elena,Lebrun, Marie-Eve,Bedard, Anne-Catherine,Seguin, Catherine,Beauchemin, Andre M.
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supporting information; experimental part
p. 17893 - 17906
(2009/07/18)
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- Facile conversion of acetals to nitriles
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Aliphatic and aromatic acetals are easily and efficiently converted to the corresponding nitriles by reaction with hydroxylamine hydrochloride in refluxing absolute ethanol.
- Yamauchi
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p. 2042 - 2043
(2007/10/02)
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