6832-88-8Relevant academic research and scientific papers
Electrophilic nitration of electron-rich acetophenones
Malecki, Natacha,Carato, Pascal,Houssin, Raymond,Cotelle, Philippe,Henichart, Jean-Pierre
, p. 1601 - 1606 (2007/10/03)
It is demonstrated that electron-rich disubstituted acetophenones react according to various electrophilic nitration conditions that generally lead to ipso substitution accompanying the conventional reaction. The hydroxy substituent does not seem prone to
A Combined Experimental and Theoretical Approach toward the Development of Optimized Luminescent Carbostyrils
Strohmeier, Gernot A.,Fabian, Walter M. F.,Uray, Georg
, p. 215 - 226 (2007/10/03)
The synthesis and photophysical data of new carbostyrils (quinoline-2(1H)-ones) with the longest hitherto observed absorption- and emission wavelengths are described. Introduction of 6-amino, 7-MeO, and 4-(CF3) substituents enabled us to rise the absorption and fluorescence maxima up to 414 and 557 nm, respectively. Supported by semi-empirical and ab initio calculations, the 6,7-(1,4-diazine)-fused carbostyril 23b displayed absorption maxima at up to 440 nm, with quantum yields of up to 0.9 and large Stokes shifts (> 100 nm), comparable to the best coumarin chromophores known. The new fluorophore is neither pH-sensitive between pH 6 and 10 nor susceptible to O2 quenching. At pH 3, the emitted light appears greenish-white, which arises from three different stages of protonation.
Dynamic Behavior of Photoexcited Solutions of 4-Nitroveratrole Containing OH(1-) or Amines
Eijk, Alexander M. J. van,Huizer, A. Herbert,Varma, Cyril A. G. O.,Marquet, Jorge
, p. 88 - 95 (2007/10/02)
Kinetics and mechanism of the photoinduced reactions of 4-nitroveratrole (NV) with OH(1-) and a number of aliphatic amines have been studied by laser kinetic spectroscopy and by measurement of transient changes in electrical conductivity.In the case of OH(1-) only reactions with NV in its lowest triplet state (T0) are observed and these lead to substitution of the OCH3 group at atom C(2) of the aromatic molecule and to formation of a number of transient ?-complexes, which return to NV.In the case of the amines both excited singlet state and triplet state reactionsare observed.The singlet state reactions with methylamine and with n-hexylamine lead to substitution of the OCH3 group at atom C(2).Although piperidine quenches the excited singlet states involved, this does not lead to substitution at C(2).The triplet state reactions with the amines start with a discrete electron-transfer reaction in which the radical anion (E) of NV is formed.Subsequent reaction of E with the radical cation of the amine leads to substitution at C(1) and to a number of ?-complexes, which return to NV.
ON THE REGIOSELECTIVITY OF THE NUCLEOPHILIC AROMATIC PHOTOSUBSTITUTIONS OF 4-NITROVERATROLE. A THREEFOLD MECHANISTIC PATHWAY.
Cantos, Albert,Marquet, Jorge,Moreno-Manas, Marcial,Castello, Assumpta
, p. 2607 - 2618 (2007/10/02)
4-Nitroveratrole (NVT) is photosubstituted with primary amines, piperidine and hydroxide ion.Primary amines and hydroxide ion cause replacement of the methoxy group in meta position with respect to the nitro group whereas piperidine photosubstitutes the methoxy group in para to the nitro group.Photoreactions with piperidine and hydroxide ion involve attack of the amine upon a triplet excited state of NVT.Mechanistic evidences indicate that the reaction with hydroxide ion is probably a SN23Ar* process whereas the reaction with piperidine involves a radical ion pair formed via electron transfer from the amine to a triplet excited state.Photoreactions with primary amines involve attack of the amine upon a singlet excited state of NVT (SN21 Ar* process).These results are discussed and justified in the context of nucleophile ionization potential considerations and ground state donor-acceptor complex formation abilities.
Reaction de l'amino-2 nitro-5 phenol et du diamino-2,5 phenol avec quelques acides et esters α-cetoniques. Synthese d'amino-7 benzoxazines-1,4 ones-2
Bris, Marie-Therese Le
, p. 551 - 555 (2007/10/02)
Our objective was the preparation of fluorescent dyes in the 1,4-benzoxazinone series; accordingly, reactions of α-ketoacids and esters with 2-amino-5-nitrophenol and 2,5-diaminophenol were investigated.With 2-amino-5-nitrophenol, ethyl pyruvate yields th
