114568-54-6Relevant articles and documents
ON THE REGIOSELECTIVITY OF THE NUCLEOPHILIC AROMATIC PHOTOSUBSTITUTION. THE PHOTOREACTION OF 4-NITROVERATROLE WITH n-HEXYLAMINE.
Cantos, Albert,Marquet, Jorge,Moreno-Manas, Marcial
, p. 4191 - 4194 (1987)
4-Nitroveratrole is photosubstituted with n-hexylamine giving rise to two isomeric anilines, N-hexyl-2-methoxy-5-nitroaniline and N-hexyl-2-methoxy-4-nitroaniline.Mechanistic evidence indicates that the first is produced in an SN2Ar* reaction through singlet and triplet excited states, whereas the second arises from a radical ion pair via electron transfer from the amine to a triplet excited state.
Photosubstitution-photoreduction mechanistic duality in the SET photoreactions of nitrophenyl ethers with amines. The role of the steps that follow the ET
Mir, Miquel,Marquet, Jordi,Massot, Oriol
, p. 12603 - 12614 (2007/10/03)
Nitrophenyl ethers are photoreduced by primary amines in water through a mechanism initiated by single electron transfer that is in direct competition with the single electron transfer photosubstitution mechanism (S(N)Ar*-SET). Our results indicate that the preferred pathway does not depend on the electron donor or proton donor ability of the amine. The key factor that determines the progress of the photoreaction is the structure of the carbon skeleton of the amine, particularly the type of hydrogens on the carbon α to the amino group. A mechanistic rationale that includes hydrogen atom transfer as a key step is discussed.
THE SEARCH FOR NEW BIOCHEMICAL PHOTOPROBES. II. THE NUCLEOPHILIC PHOTOSUBSTITUTION OF 2-FLUORO-4-NITROANISOLE.
Pleixats, R.,Figueredo, M.,Marquet, J.,Moreno-Manas, M.,Cantos, A.
, p. 7817 - 7826 (2007/10/02)
The photosubstitutions of 2-fluoro-4-nitroanisole with several amines are studied.The preparative results, the thermal stability of the photochemical substrate, and the limiting quantum yield values obtained from photoreactions with several nucleophiles suggest the possible usefulness of 2-fluoro-4-nitrophenyl ethers as biochemical photoprobes.