Pure Appl. Chem., 2010, Vol. 82, No. 9, pp. 1761-1771
http://dx.doi.org/10.1351/PAC-CON-09-08-08
Published online 2010-06-19
Proximity-assisted cycloaddition reactions of ω‑azido cyanohydrin ethers: Synthesis of diversely functionalized bicyclic tetrazoles
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.