15313-94-7Relevant academic research and scientific papers
Thermal decomposition of N-acyloxy-N-alkoxyamides a new HERON reaction
Johns, Jennifer P.,Van Losenoord, Arjan,Mary, Clement,Garcia, Pierre,Pankhurst, Damian S.,Rosser, Adam A.,Glover, Stephen A.
experimental part, p. 1717 - 1729 (2011/09/20)
The HERON reaction has been observed in the thermal decompositions of N-acyloxy-N-alkoxyamides 1b, members of the class of anomeric amides. The N,N-bisoxo-substitution results in reduced amide resonance and this, combined with an nO-σ*NOAcyl anomeric destabilization of the N-OAcyl bond, results in their intramolecular rearrangement to anhydrides 42 and alkoxynitrenes 43 in competition with homolysis of the N-OAcyl bond to alkoxyamidyls 51. The primary HERON product alkoxynitrenes are scavenged by oxygen, giving a nitrate ester, in competition with a rearrangement to nitriles and dimerization to hyponitrites, leading, under the conditions, to alcohols and aldehydes. Persistent alkoxyamidyls most likely form a 1,3-diradical in a solvent-cage reaction, which cyclizes to 3,5-disubstituted-(5H)-1,4,2-dioxazoles 47. Substituent effects support this competition reaction. CSIRO 2010.
Establishment of heterolytic and homolytic Y-NO2 bond dissociation energy scales of nitro-containing compounds in acetonitrile: Chemical origin of NO2 release and capture
Li, Xin,Zhu, Xiao-Qing,Zhang, Fan,Wang, Xiao-Xiao,Cheng, Jin-Pei
, p. 2428 - 2431 (2008/09/20)
(Chemical Equation Presented) The first heterolytic and homolytic N(O)-NO2 bond dissociation energy scales of three types Y-nitro (Y = N, O) compounds and corresponding radical anions in acetonitrile were established by using titration calorimetry combined with relevant electrochemical data through proper thermodynamic cycles.
Anionic Surfactants Catalysis in the Two-phase Oxidation of Toluene Derivatives with Cerium Ammonium Nitrate. A Facile Synthesis of Some Benzaldehydes
Skarzewski, Jacek,Mlochowski, Jacek
, p. 963 - 967 (2007/10/02)
The catalytic activity of sodium 1-dodecanesulfonate, sodium dodecyl sulfate, disodium 2-dodecyl-1,3-propanediyl disulfate (1) and trisodium 2,2-bis(sulfonatemethyl)tetradecylsulfate(2) was tested in the two-phase oxidation of p-xylene with cerium ammonium nitrate (CAN).Also various tolouene derivatives were oxidized with CAN in the presence of sodium dodecyl sulfate.The observed reaction enhancements are discussed in terms of the micelle-substrate interaction.The catalytic oxidation of some toluene derivatives (3) with a subsequent thermal rearrangement of the oxida tion product offers a simple synthetic route to benzaldehydes 4.
THE ROLE OF NITRATE FREE RADICALS IN THE PHOTOCHEMICAL SIDE-CHAIN NITROOXYLATION OF ALKYLBENZENES BY CERIUM(IV) AMMONIUM NITRATE IN ACETONITRILE
Baciocchi, E.,Giacco, T. Del,Rol, C.,Sebastiani, G. V.
, p. 541 - 544 (2007/10/02)
It is suggested that the reactive species in the CAN-induced photochemical side-chain nitrooxylation of alkylbenzenes is the nitrate radical, which probably acts as one-electron oxidant.
Mercury-assisted solvolyses of alkyl halides. Simple procedures for the preparation of nitrate esters, acetate esters, alcohols and ethers
McKillop,Ford
, p. 2467 - 2475 (2007/10/05)
The reactions of a wide variety of alkyl halides with mercury(I) and/or (II) nitrate in 1,2-dimethoxyethane, mercury(II) acetate in acetic acid, aqueous mercury(II) perchlorate, and mercury(II) perchlorate in alcohol solvents have been investigated; as a result, simple high yield procedures for the conversion of alkyl halides into the corresponding nitrate esters, acetate esters, alcohols and ethers have been developed.
