Author Topic: Epoxide/sodium azide reaction yields a-azidohydrin  (Read 725 times)

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Epoxide/sodium azide reaction yields a-azidohydrin
« on: September 27, 2002, 09:54:00 AM »
Aryl-substituted epoxides react with aqueous sodium azide to form a-azidohydrins, NOT B-azidohydrins.  This is according to the following journal references:

JOC, 1999, 64, 6094-6096
"Ring Opening of Epoxides with Sodium Azide in Water.  A Regioselective pH-Controlled Reaction"

JOC, 1993, 58, 2663-2669
"Acid-Catalyzed Hydrolysis of cis- and trans-Anethole Oxides:  Discrete Carbocation Intermediates and Syn/Anti Hydration Ratios"

Thank you