- Access to Cyanoimines Enabled by Dual Photoredox/Copper-Catalyzed Cyanation of O-Acyl Oximes
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An efficient strategy for the synthesis of pharmaceutically important and synthetically useful cyanoimines, as well as cyanamides, has been described. This strategy is enabled by dual photoredox/copper-catalyzed cyanation of O-acyl oximes or O-acyl hydroxamides. This state of the art protocol for cyanoimines and cyanamides features readily available starting materials, mild reaction conditions, good functional group tolerance, and operational simplicity. The resultant cyanoimines can be transformed into structurally diverse and functionally important N-containing heterocycles.
- Wei, Ziyan,Yu, Shouyun,Zhang, Ai Hua,Zhang, Hao
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supporting information
p. 7315 - 7320
(2020/10/02)
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- Process for the preparation of aldehydes and ketones
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A process for the preparation of vinyl, alkynyl or aryl aldehydes or vinyl, alkynyl or aryl ketones includes reacting vinyl-, alkynyl- and aryl- and -methylene compounds with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, heterocyclic or aromatic NO or NOH containing compounds.
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- Solvent effects on homolytic bond dissociation energies of hydroxylic acids
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The homolytic bond dissociation energies (BDEs) of the O-H bonds in DMSO solution for (a) phenol and a number of its derivatives, (b) three oximes, (c) three alcohols, (d) three hydroxylamines, and (e) two hydroxamic acids have been estimated by eq 1: BDE(HA) = 1.37pK(HA) + 23.1E(ox)(A-) + 73.3 kcal/mol. For most of these hydroxylic acids, the BDEs of the O-H bonds estimated by eq 1 are within ±2 kcal/mol of the literature values in nonpolar solvents or in the gas phase. There is no reason to believe, therefore, that these BDEs are 'seriously in error because of failure to correct for solvent effects' as has been claimed on the basis that BDEs in highly polar solvents estimated for the O-H bond in phenol by photoacoustic calorimetry must be so corrected.
- Bordwell, Frederick G.,Liu, Wei-Zhong
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p. 10819 - 10823
(2007/10/03)
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- Reaction of 2-nitroso-2-methyl propane with formaldehyde, glyoxylate and glyoxylic acid
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2-nitroso-2-methyl propane reacts with formaldehyde, glyoxylate, glyoxylic, pyruvic and phenylglyoxylic acid giving the corresponding N-t-butyl hydroxamic acids. These reactions involve formation of the dipolar addition intermediates and 2-nitroso-2-methyl propane acts as a nucleophile in the reaction step in which these intermediates are formed.
- Pilepic, Viktor,Ursic, Stanko
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p. 7425 - 7428
(2007/10/02)
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- The Thermal Decomposition of N,O-Diacyl-N-t-butylhydroxylamines
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Several N,O-diacyl-N-t-butylhydroxylamines and O-acyl-N-t-butylhydroxylamines were prepared, and their thermal decompositions were studied.The thermal decompositions of N,O-diacyl-N-t-butylhydroxylamines in tetralin gave substituted N-t-butylbenzamides, carbocyclic acids 1,1'-bitetrayl, and 1,2-dihydronaphtalene as the major products, together with small amounts of carbon dioxide, t-butylamine, and benzanilides.In the thermal decompositions of O-acyl-N-t-butylhydroxylamines, the products were t-butylamine, carbocyclic acids, substituted N-t-butylbenzamides, 1,1'-bi tetrayl, and 1,2-dihydronaphtalene.
- Uchida, Yuzuru,Hashimoto, Yukinobu,Kozuka, Seizi
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p. 2309 - 2314
(2007/10/02)
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