Synthesis and Characterization of Phosphomacrocycles on the Basis of 2,7-Dihydroxynaphthalene

Pavel V. Slitikov,^a@ Yuliya B. Evdokimenkova,^b Еlena N. Rasadkina,^cLarisa К. Vasyanina,^с and Eduard Е. Nifantiev^с

^aBauman Moscow State Technical University, 105005 Moscow, Russian Federation
^bZelinsky Institute of Organic Chemistry RAS, 119991 Moscow, Russian Federation
^cMoscow Pedagogical State University, 119021 Moscow, Russian Federation

^@Corresponding author E-mail: pavlasiy@mail.ru

Macroheterocycles 2011 4(4) 311-323

DOI: 10.6060/mhc2011.4.07

Received 04.07.2011
Accepted 15.10.2011

Phosphorus containing macrocycles on the basis of 2,7-dihydroxynaphthalene and amides of phosphorous acid were synthesized. The molecular assembly technique for the preparation of “uniform” naphthaphosphacyclophanes (containing only residues of 2,7-dihydroxynaphtalene) and “nonuniform” naphthaphosphacyclophanes (containing different naphthylene residues with hydroxy groups located in different aromatic rings) is proposed. Their properties were studied and the computer MM2 optimizations of molecular geometry were carried out. A method for the preparation of phosphorus containing macrocycles with three or four regularly exchanging 2,7-dihydroxynaphtylene and phosphorus acid residues was proposed. Their oxidation and sulfur addition were also studied. Individual character and structure of all synthesized systems were proved unambiguously by TLC, 31P, 13C and 1H NMR spectroscopy, elemental analysis and MALDI-TOF mass-spectrometry.

Keywords: 2,7-Dihydroxynaphthalene, triamidophosphites, molecular assembly, macroheterocycles, naphthaphosphacyclophanes, phosphocrown ethers.

MHC2011_t04n04_311-323.pdf (1.06 MB)

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