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Pure Appl. Chem., 2010, Vol. 82, No. 9, pp. 1761-1771

Published online 2010-06-19

Proximity-assisted cycloaddition reactions of ω‑azido cyanohydrin ethers: Synthesis of diversely functionalized bicyclic tetrazoles

Stephen Hanessian*, Benoît Deschênes-Simard, Daniel Simard, Caroline Chenel, Edgar Haak and Vlad Bulat

Department of Chemistry, University of Montréal, C.P. 6128, Succ. Centre-ville, Montréal, QC, H3C 3J7, Canada

Abstract: Aliphatic azidonitriles separated by three or four carbon atoms undergo facile cyclo-additions in the presence of BF3·OEt2 at room temperature or lower, to give bicyclic tetrazoles. 1-Azido-[2-aryl-1,3-dioxolanyl]-glycerols afford oxabicyclic tetrazoles with trimethylsilyl cyanide (TMSCN). Aspects of these facile proximity-induced 1,3-dipolar cycloadditions are discussed with mechanistic interpretations.