Direkte Oxidation von Aziden zu Nitroverbindungen

Abstract

„Gezähmte“ Hypofluorige Säure – der Acetonitril‐Komplex HOF⋅CH3CN – hat sich als ein bequemes Reagens für die präparative Oxidation von Aziden zu den entsprechenden Nitroverbindungen erwiesen. Substrate dieser vielseitigen Methode sind sowohl aromatische wie auch aliphatische Azide.

Synthetic Procedures for the Preparation of Nitroalkanes

“…The studies of this oxidant strongly support the notion that the oxygen atom of this reagent is a very strong electrophile. This and the fact that many transformations could be accomplished only by HOF⋅CH 3 CN, and not by any other oxygen‐transfer agent, encouraged Rozen and Carmeli to examine if the carbon‐bonded nitrogen of azides would be nucleophilic enough to interact with the oxygen atom of HOF⋅CH 3 CN. Thus, thanks to the efficiency of this oxidant, a variety of azides 42 , easily obtainable from alkyl bromides and sodium azide, were converted to primary nitroalkanes 14 in very good or quantitative yields and within short reaction times (Scheme ).…”