93398-04-0Relevant articles and documents
PHOTOREACTION OF 3,4-DIMETHOXY-1-NITROBENZENE WITH BUTYLAMINE. A pH DEPENDENCE OF REGIOSELECTIVITY
Kuzmic, Petr,Pavlickova, Libuse,Velek, Jiri,Soucek, Milan
, p. 1665 - 1670 (2007/10/02)
Irradiation of 3,4-dimethoxy-1-nitrobenzene in the presence of butylamine leads to the formation of both possible photosubstitution products, i.e., 2-methoxy-4-nitro-N-butylaniline and 2-methoxy-5-nitro-N-butylaniline with the predominance of the latter.Regioselectivity of the reaction as measured by molar ratio of the two isomeric products varies with pH of the solution, ranging from 3:1 at pH 10 to 12:1 at pH 12.The results are discussed in view of possible use of 3,4-dimethoxy-1-nitrobenzene moiety as a lysine-directed photoaffinity probe.
NITROPHENYL ETHERS AS POSSIBLE PHOTOAFFINITY LABELS. THE NUCLEOPHILIC AROMATIC PHOTOSUBSTITUTION REVISITED.
Cervello, J.,Figueredo, M.,Marquet, J.,Moreno-Manas, M.,Bertran, J.,Lluch, J. M.
, p. 4147 - 4150 (2007/10/02)
The photoreactions of nitrophenyl ethers with simple primary and secondary amines show a remarkable nucleophile influence on the reaction orientation.Calculations indicate a change from charge controlled to frontier orbital controlled reactions moving from smaller to larger amines.