Preparation of macrocyclic ether–esters, thioether–esters, and ether–thiolesters

Abstract

A series of macrocyclic ether-esters, thioether-esters, and ether-thiolesters [(I )-(I O)] have been prepared by treating various oligo-ethylene glycols and sulphur-containing oligo-ethylene glycols with malonyl, succinyl. and glutaryl chlorides.WE have previously reported the synthesis 2-5 and cationcomplexing properties of several oxathiapentadecanes and thio-crown compounds. Several of the thio-(crown-5) compounds were shown to form more stable (as measured by log K ) complexes in aqueous solution with Ag+ and Hg2+ than with TI+ and Pb2+. Also, metal-ligand complexes of 1 : 2 stoicheiometry were found for the reaction of Ag+ and Hg2+ with several of the thio-crown ligands.6 We present here the synthesis of compounds (1)-(lo), containing ether, ester, thio-Preliminary communication, J.

Synthesis of macrocyclic polyether-diester compounds with an aromatic subcyclic unit

“…The assigned structures are consistent with the IR and NMR spectra and the molecular weights. Isophthalates 4-8 exhibited the expected carbonyl bands in the IR at 1715 ± 5 cm-1, the nitroisophthalates 9-13 at 1725 ± 5 cm-1, the terephthalates 14-16 at 1720 ± 5 cm-1, and the phthalates 17 and 18 at 1720 ± 5 cm-1. 34 The NMR spectra of the aromatic portion of compounds 4-8 exhibited the typical isophthalate peaks35 at 7.57 ± 0.02 (H5), a doublet at 8.25 ± 0.05 (H4 and H6) and 8.76 ± 0.06 (H2).…”

“…A satisfactory elemental analysis could not be obtained for five of the compounds (6,11,(17)(18)(19). The sulfur-containing compounds appeared to decompose as noted by the development of a distinct yellow color on standing.…”

The Preparation and Cation Complexation Properties of Macrocyclic Polyether-Diester Ligands: A Short Review

“…Proton NMR spectra for lOd and for the complex of 1M with isopropylammonium perchlorate at room temperature, -70, -30, -10 eC (coalescence temperature) and at +20 °C in CD2CIj (solvent peak at 5.25). (Bradshaw et al, 1976Bradshaw and Thompson, 1978;Maas et al, 1977).…”

Investigation of the ınhibitory effects of some macrogenetic thiocrown ethers on polyphenol oxidase enzyme

“…Tiyocrown eterlerin makrohalkalı formasyonunun karbonil grubu kapsadığı önceden biliniyordu [28][29][30][31]. Makrosilik eter-ester bileşiğinin [32], eter-ester içeren geniş kapsamlı polieter-diester bileşiğinin [33][34][35][36][37][38][39][40], tiyoeter-ester [35,37,39,41] ve etertiyolester [35,37] bileşiğinin sentezi, Bradshaw, Izatt ve Christensen tarafından dibazik asit tuzu ve alfa, omega-dihalo bileşikleri veya dibazik asit klorürleri ve alfa, omegadihidroksi bileşiklerinden herhangi birine bağlanarak hazırlanmıştır. İki makrohalkalı polieter-monoester bileşikleri, Matsushima [42] tarafından normal verimlilikle bulunmuştur.…”