Ebrahim Abouzari-Lotf - BINOL aza macrocycle derivatives: Synthesis of dinaphthosulfone aza macrocycles using p-toluenesulfonic acid (p-TsOH) in methanol as an efficient route and evaluation of their 1H NMR spectra

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      Rostami, E., Shockravi, A., Fattahi, H., Heydarian, D., Minaee,   S.S., Naghdi, S., Lotf, E.A., Sadeghpour, M., Hosseini, H.,   Taheri, Z., Ghorbani, S., Javadi, A., Ataei, S.M. 184  (8) 2066-2077

      Abstract: Dinaphthosulfone aza macrocycles were   synthesized from the reaction of diamines and dinaphthosulfone   diester (1,1'-sulfoxobis-(2-naphthoxy(2-methyl acetate))) in   methanol in the presence of catalytic amounts of para   toluenesulfonic acid (p-TsOH). Dinaphthosulfone diester   (1,1'-sulfoxobis-(2- naphthoxy(2-methyl acetate))) was   synthesized from the corresponding dinaphthosulfide diester and   hydrogen peroxide in formic acid at room temperature.   Dinaphthosulfide diester was prepared from initial   dinaphtholsulfide diol (1,1'-thio bis(2-hydroxy naphthalene)) and   methylchloroacetate. 1H NMR spectroscopy showed the unusual   splittings for these dinaphthosulfone aza macrocycles, and this   finding could be proposed as the role of tetrahedral structure of   sulfone functional group, hydrogen bonding in the cavity and size   of macrocycle.

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