109057-09-2Relevant academic research and scientific papers
Synthesis and cycloaddition of N-substituted pyrroles with polyfluorinated substituents
Moiseev,Vasil'ev
, p. 1948 - 1953 (2007/10/03)
Reactions of N-pyrrolylpotassium with fluorinated electrophiles yielded N-substituted pyrroles containing polyfluoroalkyl, polyfluoroalkenyl, polyfluoroalkylsulfonyl, and polyfluoroaryl substituents. N-Polyfluoro- substituted pyrroles did not isomerize at ≥100°C; they were found to be reactive in [4+2] cycloaddition reactions with perfluorobut-2-yne.
Electrophilic Hydrogen-Deuterium Exchange of Some Deactivated Pyrroles
Gilow, Helmuth M.,Hong, Yoon H.,Millirons, Paula L.,Snyder, Richard C.,Casteel, William J.
, p. 1475 - 1480 (2007/10/02)
The rate coefficients and partial rate factors for the hydrogen-deuterium exchange of some 1-substituted pyrroles (1-substituents= -COCH3, -COC6H5, -SO2CH3, -SO2CF3, -N(1+)(CH3), -N(1+)H(CH3)2, -SO2C6H5) in deuterated trifluoroacetic acid have been determined.In all cases the rate of exchange is faster at the 2-position.Similary, the hydrogen-deuterium exchange of some pyrroles with electron withdrawing substituents in the 2-position indicate a relative reactivity of 4->5->3-position with the selectivity being greatest for the more electron withdrawing groups.A nitro group in the 3-position of pyrrole shows a relative reactivity of 5->2->4-position for the hydrogen-deuterium exchange in deuterated trifluoroacetic acid.A linear correlation is observed for the log of the rate coefficient of the hydrogen-deuterium exchange at the 4-position of some 2-substituted pyrroles and the difference in the calculated energy of formation of the pyrrole and the corresponding 4-deuterated cation.
