18226-18-1Relevant academic research and scientific papers
Spectroscopic and Kinetic Study of an Intramolecular Aromatic Nucleophilic Photosubstitution. Reaction Mechanism of a Photo-Smiles Rearrangement
Yokoyama, Kenji,Nakagaki, Ryoichi,Nakamura, Junko,Mutai, Kiyoshi,Nagakura, Saburo
, p. 2472 - 2475 (1980)
Photo-Smiles rearrangement reaction of N-aniline was studied by measuring the absorption spectra of transient species.Two intermediates A and B were observed and were assigned to a solvated ion pair and the Meisenheimer complex, r
Photoinduced Intramolecular Aromatic Nucleophilic Substitution (the Photo-Smiles Rearrangement) in Amino Ethers
Mutai, Kiyoshi,Kobayashi, Keiji
, p. 462 - 465 (1981)
Intramolecular rearrangement was induced by light as well as base in a homologous series of 1-(p-nitrophenoxy)-ω-anilinoalkanes, p-O2NC6H4O(CH2)nNHPh(n=2-5), yielding N-(p-nitrophenyl)-ω-anilino-1-alkanols, p-O2NC6H4N(Ph)(CH2)nOH.The reaction rate in acet
Competitive Catalysis and Quenching by Amines of Photo-Smiles Rearrangement as Evidence for a Zwitterionic Triplet as the Proton-Donating Intermediate
Wubbels, Gene G.,Sevetson, Bradley R.,Sanders, Houston
, p. 1018 - 1022 (1989)
Ten amine bases are observed to catalyze the photo-Smiles rearrangement of 4-O2NC6H4OCH2CH2NHPh in acetonitrile.Plots of (quantum yield)-1 vs -1 are linear for all ten bases, but the intercepts representing limiting quantum yi
Bifunctional Reactivity of the Nitrophenoxyl Group in Intramolecular Photoreactions
Mutai, Kiyoshi,Tukada, Hideyuki,Nakagaki, Ryoichi
, p. 4896 - 4903 (2007/10/02)
The photochemical behavior of a homologous series of compounds, p-O2NC6H4O(CH2)nNHPh (n = 2-10, 12, and 16) in acetonitrile is reported.The lower (n = 2-6) homologues undergo an apparently nucleophilic type rearrangement to give ω-((p-nitrophenyl)amino)al
EFFECT OF α-CYCLODEXTRIN COMPLEXATION ON A GENERAL-BASE-CATALYZED PHOTO-SMILES REARRANGEMENT
Wubbels, Gene G.,Sevetson, Bradley R.,Kaganove, Steven N.
, p. 3103 - 3106 (2007/10/02)
α-Cyclodextrin complexation suppresses the efficiency of base-catalyzed photo-Smiles rearrangement of p-O2NC6H4OCH2CH2NHPh by 80percent in aqueous solution. α-CD does not restrict the electron transfer; it inhibits by enhancing the decay of an intermediat
PHOTO-SMILES REARRANGEMENT (IV) ELECTRON-TRANSFER MECHANISM OF AN INTRAMOLECULAR AROMATIC NUCLEOPHILIC SUBSTITUTION
Nakagaki, Ryoichi,Hiramatsu, Mitsuo,Mutai, Kiyoshi,Nagakura, Saburo
, p. 69 - 76 (2007/10/02)
The mechanism of the photo-Smiles rearrangement involves formation of an intramolecular radical ion-pair and a spiro-type Meisenheimer complex.The complete reaction pathways can be qualitatively described by the use of potential energy surfaces for the gr
