Direct synthesis of organic azides and thiols derived from ethylene glycol via modified Appel reaction
Journal Title: CHEMIK nauka-technika-rynek - Year 2014, Vol 68, Issue 7
Abstract
Classical method of conversion of primary alcohols into corresponding alkyl halides by usage of triphenylphosphine and tetrahalogenated methane, so-called Appel reaction, was adopted for the direct synthesis of terminal organic thiols and azides derived from ethylene glycol and its sulfurated analogue. In key step of the presented ‘one-pot’ protocol, corresponding dibromides, generated in situ via reaction with N-bromosuccinimide (NBS), were converted into desired products by treatment with appropriate sulfur or nitrogen nucleophile. A series of diazides and dithiols derived from (poly)ethylene glycols and their sulfur analogues were obtained. Selected diazides were utilized for the construction of novel macrocyclic systems, that were tested incontext of their complexing properties.
Authors and Affiliations
M Stefaniak, K Urbaniak, J Romański, P Seliger, N Gutowska
Keywords
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