a Institut für Organische Chemie der Universität Hamburg, Martin-Luther-King-Platz 6, D-20146, Hamburg, Germany
b Departamento de Química, Universidade Federal de Santa Maria, 97100-900, Santa Maria-RS, Brazil
Abstract:
When 2,6-di-O-tert-butyldimethylsilylated cyclomalto-oligosaccharides (cyclodextrins) are treated with allyl or methyl iodide and NaH in dry tetrahydrofuran, O-2 → O-3 migration of the secondary 2-O-tert-butyldimethylsilyl groups occurs, leading to 2-O-alk(en)yl-3,6-di-O-tert-butyldimethylsilyl-cyclodextrin derivatives. The detection and identification of the reaction step during which migration occurred is described and possible mechanisms of migration are discussed.