Nikolay G. Lukyanenko

Bis(fluorenono)phanes: a new class of perspective macrocyclic receptors

Two representatives of a novel class of cyclophanes containing two fragments of 2,7-dioxy-9H-fluoren-9-one bridged by triethylene glycol and p-xylyl linking units have been prepared. X-Ray analysis shows that the former has an anti-conformation and the cavity is self-filling with fluorenone moieties.

Novel cryptands containing thiourea units as a part of the macrocyclic framework

Alkylation of diaza-18-crown-6 by N-substituted phthalimides having a terminal halogen in the substituent, and subsequent product interaction with hydrazine hydrate and acid hydrolysis gave corresponding N,N′-disubstituted diaza-18-crown-6 compounds with terminal primary amino groups in the side chains. The reaction of these compounds with carbon disulfide or with appropriate bis[oligo(ethyleneoxy)]isothiocyanates afforded a series of novel cryptands with one or two thiourea units in one of the bridges.

Macroheterocycles. Part 42. A facile synthesis of dihydroxy cryptands and their dehydroxylation

A facile synthesis of hydroxy cryptands by the reaction of diglycidyl ethers with a diazacrown ether is reported. The reaction results in a mixture of bi- and tri-cyclic cryptands which can be separated by chromatography. The yield of bicyclic cryptands is lowered with a decrease in the diazacrown ether cycle size and an increase in the number of oxyethylene moieties between the epoxy groups in the diglycidyl ether. The results are interpreted in terms of the intramolecular hydrogen bonding of epoxy groups promoting the steric fixation of the reaction centres. Dehydroxylation of the bicyclic dihydroxy cryptands has been performed by means of chlorination followed by reduction.