16857-92-4Relevant articles and documents
The Hydrolysis of 1,3,5-Tripyrrolidinobenzene
Knoche, Wilhelm,Vogel, Siegmund
, p. 1937 - 1942 (1988)
In acidic solutions 1,3,5-tripyrrolidinobenzene (TPB) and methyl-TPB hydrolyse forming 3,5-dipyrrolidinophenol (DPP) and methyl-DPP, respectively.The reaction proceeds by two successive protonations on carbon atoms of the aromatic ring followed by hydrolysis.The reaction mechanism is described, and the protonation equilibria of TPB and DPP are determined.
Hydroxy- and Methoxybenzene Derivatives with Benzenediazonium Salts ― Chemical Behavior and Tautomeric Problems
Micheletti, Gabriele,Boga, Carla,Forlani, Luciano,Del Vecchio, Erminia,Zanna, Nicola,Mazzanti, Andrea,Monari, Magda
supporting information, p. 964 - 974 (2017/02/15)
The azo-coupling reactions between 4-nitrobenzenediazonium tetrafluoroborate and a series of benzene derivatives bearing at least one electron-donating hydroxy or methoxy substituent have been studied. Depending on the nucleophile and its relative ratio with the diazonium salt, it was possible to obtain mono- and disubstituted products as well as a trisubstituted product for phloroglucinol. The reactions between 3,5-diaminoanisole or 3,5-diaminophenol derivatives and 2 equiv. of diazonium salt gave the monosubstituted product in the first case and a diadduct in the second case; X-ray diffraction analysis revealed a highly symmetric structure for the latter. The different behaviors of hydroxy- and methoxy-substituted compounds was particularly evident for phloroglucinol and 1,3,5-trimethoxybenzene and may be rationalized on the basis of the different electronic effects of the substituents. The propensities of the aromatic rings to undergo H/D exchange reactions were investigated for a series of substrates, and a comparison of the results obtained provided new insights into this phenomenon and permitted a better explanation of the findings reported here; a new particular interaction competes with the formation of a proton–phloroglucinol σ complex.
