Categories: C-N Bond Formation > Synthesis of azides >
Synthesis of 1,2-azido alcohols
Recent Literature

An efficient ring opening of epoxides and aziridines has been carried out at
room temperature using poly(ethylene glycol) (PEG-400) as reaction medium to
form the corresponding 2-azido alcohols and 2-azido amines, respectively, in
excellent yields within 30-45 minutes and with high regio- and stereoselectivity.
B. Das, V. S. Reddy, F. Tehseen, M. Krishnaiah, Synthesis, 2007,
666-668.

A wide variety of epoxides and aziridines were converted to the
corresponding β-azido alcohols and β-azido amines with sodium azide using
OxoneŽ in aqueous acetonitrile. The reactions were highly regioselective and
efficient with excellent yields at room temperature under mild reaction
conditions.
G. Sabitha, S. R. Babu, M. S. K. Reddy, J. S. Yadav, Synthesis,
2002, 2254-2258.

A convenient, efficient, and highly regioselective synthesis of 1,2-azidoalcohols and 1,2-azidoamines in excellent
yields has been achieved by using cerium(III) chloride and
sodium azide for a mild ring opening of epoxides and aziridines.
G. Sabitha, R. S. Babu, M. Rajkumar, J. S. Vadav, Org.
Lett., 2002, 4, 343-345.

Aldehydes are safely and conveniently converted to acyl azides and benzyl
ethers to azido ethers by treatment with polymer supported iodine azide in MeCN
at 83 °C. The reaction provides an alternative to the use of iodine azide in
radical azidonations.
L. G. Marinescu, C. M. Pedersen, M. Bols, Tetrahedron, 2005,
61, 123-127.
