Abstract

We previously found that cyclophosphorylation at the secondary hydroxy groups of β-cyclodextrin silyl derivative I with phenylphosphonous dichloride II is unexpectedly accompanied by an appreciable desilylation [1]. Based on some experimental data, we suggests that the desilylation act (second phase) is preceded by a specific supramolecular reorganization of the intermediately formed conjugate [chemically bound cyclodextrin derivative I (host) and chlorophosphonite residue II (guest) (stage I)]. According to the H, C, and Р NMR data, the desilylation does not occur when this reaction is carried out in the presence of two molar equivalents of adamantane. Along with cyclophosphorylated moiety (l = 1), in this case a large number of noncyclophosphorylated residues (m = 3) attached to the cyclodextrin backbone is formed, which contain also the included adamantine. After sulfur addition to compound III, the inclusion complex with adamantane was isolated by column chromatography. DOI: 10.1134/S1070363211020290

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